


Follow You Down

by Skyrogue



Category: Supernatural
Genre: Abduction, Angst, Baker!Dean, Bombing, Enemies to Lovers, Fluff, Graphic violence will include:, Kinda, M/M, Mafia AU, Minor Character Deaths, Mixed feelings, Threats And Intimidation, mobster!Castiel, mostly off screen torture, shoot outs, warnings will be posted to appropriate chapter summaries
Language: English
Status: In-Progress
Published: 2020-02-28
Updated: 2020-03-25
Packaged: 2021-02-28 00:02:01
Rating: Mature
Warnings: Graphic Depictions Of Violence
Chapters: 6
Words: 25,382
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22944466
Author URL: https://archiveofourown.org/users/Skyrogue/pseuds/Skyrogue
Summary: Dean Winchester—Chicago resident, small business owner, classic car enthusiast—never intended to have ties to the Chicago Gospel mafia until one Castiel Novak enters his café and threatens to break his knees. What comes next is a whirlwind of romantic dates, illegal activities, and being the target of a rival mafia, the Chicago Omens.
Relationships: Dean Winchester/Castiel, Sam Winchester/Jessica Moore, previous Dean Winchester/Benny Lafitte
Comments: 33
Kudos: 107





	1. Chapter 1

**Notes for the Chapter:**

> Alrighty, kids, put on your seatbelts, because I’m about to floor it down the mafia au highway.
> 
> The first two chapters are short and very awkward/stiff, and I’d like to apologize for that. Just stick with it, I promise my stupid writing gets better in the third chapter.
> 
> Anywho, I’ll try my best to update this story every couple days (or once a week at the very most). Subscribe to receive emails when I post new chapters and follow me at prayedtoyou.tumblr.com for more SPN/Destiel content!
> 
> **Chapter warning: threats and intimidation.**

“You’re _sick_?” Dean asks into the phone, frowning. _Who gets sick in the middle of July?_

“Yeah...” Garth weakly confirms. “I think it’s some kind of stomach bug. I haven’t been able to keep anything down all day.”

Dean bites his lip. _Fuck_ , he thinks. Claire requested the day off two weeks ago and now Garth is sick. His only two managers are unavailable, so Dean will have to stay all night. It’s only noon, six hours into his shift, and he has nine more hours to go. He scrubs a hand down his face, already tired and wanting to go home.

“Alright. Well, there’s not much we can do about it, so just get some rest and feel better. I’ll see you back here Saturday, right?”

“Yeah, I should be fine by Saturday.” Garth sighs through the phone. “I’m really sorry, Dean, I’d be there if I could.”

Normally when people call in sick, Dean can pick out their bullshit from a mile away. But Garth has never called in sick before, not in his three years working at Dean’s café. If he’s calling off now, it must be serious. “Don’t sweat it, man. Take care of yourself.”

They exchange goodbyes and hang up. Dean shakes his head.

It’ll be a fifteen hour day for him. Normally, Dean shows up six days a week at six in the morning and stays until four, but on days like today, he’s forced to work open to close. He’s bitter about it, but he knows what he signed up for.

Dean opened (Don't Fear) The Java six years ago after graduating college and spending a few years at a bakery, learning the ins and outs of the culinary business. He knew the disadvantages long before he started: long hours, low income during the start up, an 80% chance the café wouldn’t make it past its first five years, and picking up the slack when his employees can’t come in. The good definitely outweighs the bad, though. Seeing people enjoy his food, reading the nice reviews online, making enough money to live on his own and send extra cash to his mom when he could. He’d work open to close every day if it meant he could continue to be his own boss.

Dean gets back to the bagels he was making before Garth called. _If it’s going to be a long night,_ he thinks, _I might as well make it worth my while._

He bakes the rest of the day. Shift change comes at one and Max and Krissy come in to take over for Ronald and Kate. He covers their staggered lunch breaks when it comes time, sending each of them to the back office with a sandwich during a lull. When he gets back to the kitchen, he decides to make three more batches of muffins and to run a sale on them tomorrow so they don’t go to waste.

Eventually he runs out of things to do. He sweeps and mops again, does the dishes, stocks sixth pans of produce and meat and cheese for the front line, and then he still has three more hours before the day is done. He double checks inventory and puts in an order with his supplier, posts updates on the social media accounts, and pays some bills early.

The light of his computer hurts his eyes after a while, so he closes them for just a second. He wakes up twenty minutes later when he hears a rapping on the door. He startles, and curses at himself for falling asleep.

“Hey, Dean?” Max sticks her head in and Dean hopes she doesn't see the thin line of drool that escaped his mouth. “It’s nine o’clock. We got all our closing stuff done, but do you need anything else?”

Nine o’clock. _Finally_. Dean gives her a tired smile. “Nope, you're free to go. Have a good night.”

Max disappears and Dean rubs at his eyes. His stomach rumbles. He hasn’t eaten since eleven in the morning.

Dean gets up from his chair, stretches, and winces in pain as his back cracks loudly. A fifteen hour day plus a power nap on a discount office chair wasn’t exactly the formula for a happy body. He promises himself that he’ll leave work early tomorrow to enjoy the softness of his bed.

The front and back kitchens have both already been scrubbed clean, but he undoes Krissy’s hard work by throwing an egg and a strip of bacon down on the flattop behind the counter. He toasts a bagel, adds a slice of cheddar, and sits down at one of the tables to enjoy his creation. He moans around the first bite.

The special moment he was sharing with his sandwich is sourly interrupted by three short knocks on the front door. He glances up to find a woman and two men standing just on the other side of the glass, all dressed up in black suits and long coats, staring at him.

“We’re closed.” Dean gestures to the closed sign on the door. 

The woman, standing in front of both of the men, raises her fist and knocks again.

“ _Closed_ ,” he reiterates. He’s not normally so rude to customers who plan to give him their money, but the day had been too long and he was too tired to bother playing games. “We’ll open tomorrow at seven, you can come back then.”

The woman is still for a moment, before she reaches into her coat and pulls out a handgun.

Dean'’s eyes widen and his sandwich falls from his hands. She shoots through the door three times, barely even blinking as she breaks the glass. Dean’s ears ring, all other sounds cut off from the discharge of the bullets, and he puts his hands over his ears a second too late.

He watches as all three of them step through the metal frame, his brain processing their actions in slow motion like a bad film. His eyes flicker to the register, where he has a baseball bat hidden underneath. It might not do much when this lunatic has a gun, but he’ll be damned if he doesn’t go down without a fight.

Dean jumps to his feet and leaps toward the counter. Before he gets there, one of the men—this one tall and black and probably twice Dean’s age—grabs him around the waist and heaves him up. Dean’s slammed down onto the counter, all the air in his lungs escaping in a dramatic huff. He grunts and balls his hands into fists. He manages to connect one hit to the man’s jaw, but he’s barely affected. The man grips both of Dean's hands and holds them above his head.

“ _Let go of me, you son of a bitch_ ,” Dean demands, but the man chuckles and doesn’t release him. Dean continues to struggle, not finding purchase, until he hears a gun click next to his head.

He turns to find the woman—pale and petite with red hair—holding a pistol against his temple. He stills.

“Alright.” He swallows. “No need to get all trigger happy in here. I’ll give you whatever you want.”

The other man comes into Dean’s line of vision, bumping the woman out of the way. She steps back, gun still trained on Dean. This one is white with dark hair and a hammer in one hand. “Whatever we want?” He smiles, but it doesn’t reach his eyes, and it terrifies Dean to his very core.

“I’ve got money in the back,” he admits. There’s only a few grand back there, the rest kept in a bank account. It would hurt to lose it, but he would get by.

The man with the hammer loses his smile. “We don’t want money. We want information.”

Information? From _Dean_? What the hell did they expect him to know? All he does is run his café, listen to the same four albums, and sleep. What could he possibly be holding out from these business-professional goons? “About what?”

“We’re looking for the whereabouts of Celeste Middleton. You probably know her as Charlie Bradbury.”

_Charlie? Oh, shit, what did she get into this time?_

Charlie worked for Dean when he first started up his café, while she was still in college. They still hang out from time to time. They used to get together to watch every Game of Thrones episode when it was airing, but he hasn’t seen her since the last Star Wars movie was released. Dean knew she had some less-than-legal hobbies, but didn’t expect her to get into trouble like this. “What do you want with her?”

“You might not know this.” He leans in and traces a finger along the edge of Dean’s bottom lip. Dean flinches away from the touch, which pulls a frown from the man’s lips. “But your friend Charlie is quite the little theif. She hacked into my boss’s bank account and stole three million dollars.”

Dean’s eyes widen. Holy shit, was that a lot of money. How the hell had Charlie managed to pull that off? “Well, sucks for your boss, but I don’t know where she is.”

The man clicks his tongue a few times. “You’re lying to me, Dean. I’m going to give you one more chance, and then I’m going to start breaking things. Starting with your knees.” He lightly taps Dean’s right knee with his hammer, just enough to jolt his reflexes.

“Go to hell,” Dean spits out.

The man pauses for the briefest of moments, a look of disappointment spreading across his face. “Shame,” he says. He moves his attention down to Dean’s jean clad knees and raises the hammer above his head.

“ _Alright_!” Dean concedes. “Alright, I’ll tell you where she is!”

The man doesn’t lower the hammer, but he looks back at Dean, eyebrow raised. He silently waits for his answer.

Dean swallows the panic in his throat and decides if he’s going to do this, he’s going to go all in. “Last I knew, she lives at 883 North Marshfield Avenue. That’s all I know, I swear. I haven’t seen her in six months.”

The man smiles and lowers his hammer. He leans in close, close enough that Dean can make out three different shades of blue in his eyes, and pats Dean’s cheek. “Good boy. Now, I hope I don’t have to explain that we were never here.”

Dean shakes his head. “Never seen you before in my life.”

He looks back at the woman, her gun still in position. “I like this one. But, enough chit chat, we’ll be leaving now.”

At the same time, each of them release Dean. The man with the hammer straightens and backs up a few steps, the man holding his arms lets go, the woman slips her gun into a holster at her ribs. They retreat back toward the door, and just before they all leave, the man with the hammer turns back around.

“It was nice meeting you, Dean. Thank you for your cooperation.” He winks, and then, just as quickly as they had arrived, they were gone.

Dean gasps in a lungful of air, feeling like he hadn’t breathed the entire time they were there. Adrenaline is still pumping through his veins, fear still very present in his chest. He forces himself to calm his breathing before he throws up.

What a _fuck_ was that? What kind of people show up in suits, not even bothering to hide their faces, and demand information from some broke café owner? What kind of business were they running that their boss had three million to steal? And why were they so comfortable making threats and holding guns and taking punches?

Having more questions than answers makes his head spin. Slowly, he rises and slips off the counter. His legs shake, but they hold him up. He takes his phone out of his back pocket and sighs in relief when he finds it isn’t broken. He types out a quick message.

_> > Just had some goons come in looking for you. Watch your back, Charles._

He looks back at the door, shattered glass littering the enteryway, and cusses. As if the day hadn’t already been long enough, he’s assaulted, threatened, and left to clean up a mess. Great, just fucking _great_.

He’ll sweep up in a minute, he decides. He needs a temporary fix to the hole in his café, and knowing all the department stores are closed by now, he makes a call to the contractor who helped him when he first started his business.

“Hey, Benny. Got a favor to ask of you.”


	2. Chapter 2

“This is the place?” Uriel asks, unimpressed. “I thought she'd have better taste.”

Castiel looks out the window and sees the building, but doesn’t process it. His mind is focused on other things, like green eyes and pink lips.

Dean was nothing like he’d expected. Castiel, Anna, and Uriel staked out his café for eight hours, waiting to get him alone. From what little Castiel had seen of him through the lenses of some outdated binoculars, he had sandy hair and a charming smile and looked good in an apron. Seeing him up close and listening to that sharp tongue was a completely different experience.

Castiel was both appreciative and disappointed that Dean gave him the address he needed. He truly didn’t want to destroy those shapely legs of his, but Dean giving Charlie up so easily showed a flaw in character. A part of Castiel wants to see him again, but in this business, there is no room for men with loose lips.

Balthazar checks the address on his phone again. “883 North Marshfield, correct?” He glances into his rear view mirror to see Castiel nod. “Yup, this is the place.”

Anna and Castiel exchange a look. He shrugs.

“Let’s get looking, then.”

The building is tall, thin, and made of faded red bricks. Dean hadn’t specified a unit, so Castiel, Anna, and Uriel break off to search each one. The first unit Castiel inspects is empty. When no one came to the door after he knocked, he picked the lock and let himself into a barren apartment. The second one he checked housed an elderly woman who answered the door in her nightgown, asking him if he knew what the hell time it was.

He apologized and left. He found Uriel and Anna on the front steps.

“Old woman,” he reports.

“Single mother with two kids,” Anna says.

“A bachelor in his forties,” Uriel adds. “That weasel deliberately gave us a false location.”

“We should return to him,” Anna suggests, looking back toward the car where Balthazar is sitting patiently, “and allow Uriel to _purify_ his little café.”

Castiel considers their statements. Dean did lie to them, and if it had been anyone else, Castiel would have put a bullet through his brain without thinking twice about it. But there was something about those wild eyes and the fire in his voice and the confidence he had, even while he was pinned down and held at gunpoint. There’s something to be said about a man who can hold his own on his back.

Something blooms in his chest. Dean lied to them. While it was incredibly stupid and could easily wind him up dead, he hadn’t actually exposed Charlie. Castiel wonders if they can make a made man out of him yet.

Castiel rubs a hand over his mouth, wiping away the slight smile that was tugging at his lips. “Not tonight. I’ll deal with him tomorrow. Alone.”

“He knowingly lied to you, Castiel,” Anna points out. “If he’s smart, he’ll either run or start walking heavy. Maybe going alone isn’t a good idea.”

“I’ll handle it,” he declares. Anna and Uriel don’t try to argue this time.

— — —

The next morning, Castiel finds himself in line at (Don't Fear) The Java, waiting while a teenager in front of him changes her mind three times before deciding on a French vanilla latte and a plain bagel. When she finally moves down the counter to wait for her order, Castiel steps up.

“Good morning, what can I get for you?” the man at the counter asks. _Andy_ , his name tag announces.

“Hello. A medium coffee with two creams, please.”

Andy punches a few buttons on his tablet and reads him his total. Cas hands over a five dollar bill and dumps his change into the tip jar. The other attendant, a college-aged looking man named Kevin, pours his cream and coffee and hands it over with a smile.

“If I could bother you for a moment,” Castiel says, taking the coffee, “would you mind fetching the owner for me? I'm an acquaintance of his.”

“Sure thing,” Kevin agrees. He heads back into the kitchen and Castiel finds a window seat at a tiny table with two mismatched chairs.

The café is cute, in a quirky way. The chairs are all different colors and shapes, there’s artwork and old license plates and framed photos of Dean and his staff on the walls, and ivy plants hang from the ceiling over each table. Castiel softly runs his thumb over a few leaves from the vine hanging closest to him.

Castiel draws his hand back when he sees the kitchen door open again. Kevin returns to the lobby first, followed by Dean.

He’s somehow even more attractive than Castiel remembers him. He still has bags under his eyes, no doubt from the extra long shift Castiel knew he pulled the day prior, but it’s obvious he got some much needed rest last night. He has on new clothes, following yesterday’s theme of a flannel over a t-shirt and a pair of faded jeans. Castiel wonders if he dresses like this everyday.

Kevin points out Castiel and Dean turns to him. His face drops immediately. The reminder that Dean is technically a target hits Castiel like a punch to the gut and he straightens.

Dean visibly swallows and takes the few slow steps toward Castiel’s table. He’s wearing the same stained white apron with the company name on the front as yesterday, with a pen and sharpie hooked onto the front. Castiel thinks about how beautiful Dean would look wearing only that apron.

He finally sits. Castiel pushes away the thoughts in his head and resumes his professional demeanor.

He lets Dean sit there for a moment, watching his eyes shift from Castiel to the door behind him, the one Castiel noticed had been haphazardly boarded up. He almost feels bad about it.

“I hope I don’t have to explain why I’ve returned,” Castiel says.

Dean shakes his head, does not reply.

“I checked on that address you so willingly gave to me and did not find what I was looking for.” He tilts his head to the side and asks, already knowing the answer, “Why is that, Dean?”

Dean is silent. Castiel imagines the fear Dean is feeling at the moment, the kind of fear he felt himself back when he first joined the Gospel.

“You lied to me. I can understand why; Charlie is someone you’re tying to protect. But,” Castiel leans in closer, “you must have known the risks that come with lying to someone like me. Did you not?”

Dean pauses, then nods.

Of course he did. Castiel knew he wasn’t an idiot. While deceiving Castiel could have been the last mistake he ever made in life, he still had the nerve to make it. He admires Dean’s loyalty and ponders if that loyalty could be shared with a person like himself.

He figures he’ll give him one last chance, one last test, before he makes a decision. “Is there any reason why I shouldn’t kill you?”

Dean looks back over the counter to where his two employees are helping customers. Castiel can nearly see the gears in his head spinning. He turns back and leans forward, a challenge in his eyes. “No.”

Castiel squints.

_No?_

“Look, I lied to you because Charlie is my friend and I’d do anything for that dumbass. You want to kill me? Fine. But you’re not getting anything out of me before you do.”

Of all the possible answers Castiel imagined Dean would come up with—from begging for his life to reasoning that he has a family to caving and giving Charlie’s real address—that wasn’t one of them. Castiel makes his decision: Dean Winchester will not be harmed. The thought makes him smile.

Castiel reaches forward. Dean’s eyes track his hand and his breath hitches when Castiel plucks the sharpie from his apron. He removes the sleeve from his coffee cup and proceeds to write down an address. “I’d like you to take a personal day tomorrow. Meet me here at seven pm. Don’t be late.”

Castiel hands over the sleeve, which Dean takes hesitantly. He looks at it, then locks eyes with Castiel. “What the hell is this?”

For the first time, Castiel feels nervous. If anything goes wrong, if Dean denies him or laughs at him or explains he’s not as queer as Castiel made him out to be, Castiel would be finished. “A restaurant. Black tie required. I’d like you to join me for dinner.”

“What, like a _date_?”

Castiel considers the word. He hadn’t been on a date in years. “Yes, a date.”

Dean shifts in his seat. “Yesterday you almost broke my knees and today you want me to go on a date with you? What kind of sick game is this?”

Castiel admits to himself that his methods aren’t as rational or thought out as the next guy, but it wasn’t like he had a lot of experience with dating in his line of work. And given that the last time had gone so horribly....

“It’s no game. I found myself attracted to you, somewhat unfortunately. I really was thankful for your cooperation last night, even if I later found your information to be faulty. I would’ve hated to break you when you're so...” He lets his eyes trail down to Dean's chest and stomach, where his body disappears under the table. He’s sure that if he undressed Dean, he’d find a soft patch of skin under his belly button, but all in all, he was in much better shape that the average baker.

The image of Dean naked spurs on more visions of the man. He imagines what Dean would look like on his knees. Imagines him with a cock in his mouth. Imagines what he looks like when he's smiling or begging or biting his lip in concentration. Castiel wants to know what his skin tastes like, what his laugh sounds like, what his hugs feel like. Wants to kiss his lips and his fingers and his hips and his thighs, wants to make him sweat and moan and shatter, wants to completely rebuild him from the ground up.

Castiel puts a halt to his fantasy before he loses his resolve. When his eyes rise to Dean’s face again, he finds parted lips and flushed cheeks.

Dean averts his eyes to the sleeve in his hand. “Give me one good reason why I should show up to this.”

Cas shrugs. “I don’t have one. This isn’t a threat, I won’t return if you aren’t interested. This is a simple invitation.”

Dean shakes his head. “I don’t even know your name.”

Castiel internally knew that Dean would want to know, but the question still makes him freeze up. He doesn’t give himself enough time to panic about it, though. “Castiel.”

“No last name?”

 _Not yet_ , he thinks. He needs time to learn more about Dean and fully trust him before he hands out anymore personal information. Instead of answering, he stands. “I hope to see you soon, Dean.”

With that, he leaves Dean's café.


	3. Chapter 3

Castiel left a full ten minutes ago and Dean is still sitting at the same table, staring down at the coffee sleeve in his hand. The address on it stares back, the slanted capital letters giving him an uneasy feeling in his stomach.

Had that really just happened? Dean spent his entire morning worrying if Castiel would show back up again after he gave him the address, but never in a million years would he have thought their second meeting would end up like this. He runs his thumb over the address. It stays there. He pinches the inside of his wrist. Not a dream.

“Dean?”

Dean pulls himself out of his head and looks up to Kevin standing over him.

“Is everything okay?” he asks.

 _No,_ he wants to say. _Everything is definitely_ not _okay. Everything is_ not _fine._

“Yeah,” he says instead. “Sorry, just...zoning out.”

Kevin doesn’t look like he believes him, but doesn’t press. “Okay, well, we’re not busy right now. Is it cool if I take my lunch?”

Lunch. Right. He still has a café to run and breaks to cover and bagels to make. He gives his most convincing smile. “Sure thing, Kev.”

He covers Kevin’s lunch, then Andy’s, and retreats back into the kitchen. He does his best to clear his head and focus on baking, but those blue eyes keep popping into his mind.

Who exactly was that guy and what gave him the right to turn Dean’s world upside down? He was doing just fine on his own, running his café, minding his own business, not stealing money from rich assholes. Why the hell had he been pulled into the middle of this? Because Charlie worked for him like three years ago? Who cares? They could have gone after her coworkers or her girlfriend—not that Dean wanted Kara to be put into danger herself, but _come on_. They must have been digging at the bottom of the barrel for them to come to Dean for information.

Castiel had come in that first night with wild dark hair and a light in his eyes Dean had never seen in an another person before. _Feral_ is the word that comes to mind when he thinks about it now. But today, his hair was combed, his button down shirt was pressed, and he wore an expression of indifference over his face like a mask. That is, until Dean gave him that spiel at the end about killing him, which made Castiel smile for just a moment.

When he gets his two batches of bagels into the oven, he pulls out his phone and punches in the address. It certainly does belong to a restaurant, and a nice one at that. Dean is sure, no matter how popular or successful his café becomes, he’d never be able to afford to eat at a place like this.

Well, if the guy is offering, Dean might as well get a free meal out of it. That is, if he doesn’t murder Dean first. Or after. But would the guy really pay for Dean to eat this fancy food when he planned on killing him after desert?

It’s best not to think about it, Dean decides. Besides, he wasn’t serious, he was definitely not showing up to dinner with Castiel. He’s going to stay home, where it’s warm and safe and comfortable, and forget he ever met the guy.

He remembers the promise he made himself the day before to leave early and calls it quits at two when Claire shows up.

Going home, as it turns out, is worse than being at work. As soon as he walks in the door, his head goes wild. Does Castiel know where he lives? Did he tap Dean’s apartment? Go through his stuff? Find all of his passwords from his laptop to hack into his accounts? Did he even need Dean’s passwords to hack into his accounts? Just how powerful was this guy? And why the hell did he want to go on a date? With _Dean_? The guy could probably get with anyone he wanted.

Dean couldn’t try to pretend he wasn’t attracted to the guy. Sure, the bright eyes and dark hair and tan skin all made a great combination, but Castiel probably had a rap sheet longer than Dean’s leg. Not to mention he was a single breath away from landing Dean in the hospital—and possibly in a wheelchair—not twelve hours earlier.

The whiplash has him reaching into his cupboard for his trusty bottle of whiskey. Never mind that it’s still early afternoon; it’s not like the time has stopped Dean before. He puts on an Indiana Jones movie, sets himself up on the couch, and tries to just relax for the first time in way too long.

Of course, it doesn’t work. His shoulders are still tense, back locked up like maximum security prison, and his jaw is in a permanent clench. Half way through his first drink, his phone rings, and he’s so strung up, he jumps half way off the couch.

His muscles finally loosen up when he sees the name on the screen and his chest swells with relief.

“Sammy!” He pauses the movie and settles back into his seat, preparing for a long talk. Since Dean moved to Chicago after school, Sam and Dean made sure to call each other about once a week. Sometimes they went longer without talking, like they had recently, but the phone calls they share after those periods of time always ended up being the best. “How goes it?”

Sam sighs on the other side of the line. “You will not believe the week I've had.”

Dean laughs. What a fucking coincidence. “Tell me about it.”

“Okay.” There's a little rustling on Sam's side and Dean can picture the kid getting comfortable for whatever long-winded story he's ready to tell Dean. “So, this couple is getting a divorce and they’re the absolute _pettiest_ people I’ve ever met in my life. They’re fighting over house plants and picture frames and lamps, but they haven’t even _mentioned_ their three kids yet....”

The rest of Sam’s ramble gets lost somewhere between California and Illinois. Dean isn’t ignoring him, per se, but he isn’t listening either. He lets Sam rant about the case and mumble about how those two fuckers don’t even deserve their kids and groan at the prospect of having to deal with them again on Monday. Dean doesn’t want to tell Sam that his problems are also petty and unimportant, but Dean can’t exactly tell him about the week he’s had. 

He considers it. If there’s anyone he can tell anything to, it’s Sam. And given that he was some big shot lawyer out in San Jose meant that if Dean needed him, he could and would fly across the country in a heartbeat to get Dean out of trouble. The only thing that worried him was the very scary thought that Castiel could hear his conversation. Dean would probably be dead before Sam even got on the plane, and then Sam would be next.

“Dude, are you even listening?”

“Yeah, I’m listening,” Dean lies.

“What was the last thing I said?”

Dean tries to rack his brain. Monday? No. Something about Sam’s dog eating through his second ‘indestructible’ chew toy in the same week? That’s not it. Dean heaves out a heavy sigh. “Okay, I wasn’t listening.”

“Are you okay?”

Yet another person has noticed Dean’s lack of attention—he’s got to get better at this stuff. He pinches the bridge of his nose. “Yeah, everything’s fine. I’m just tired. I’ve had a couple long days this week.”

“You wanna talk about it?”

“No, Samantha, I don’t.” It comes out harsher than he meant for it to. He sighs again. “Sorry, I’ve just been stressed.”

“Okay. Well, how about we try this again next week? Maybe you’ll get your panties straightened out by then.”

“Bitch.”

“Jerk.” He can hear Sam’s smile in the word. “I’ll talk to you later, Dean.”

“Tell Jess I said hi.”

After they hang up, Dean gets back to his drink. When it’s finished, he pours himself another. And then another. When he finishes that one, he debates whether he should continue drinking or not. The upside is he just might be able to get drunk enough to stop thinking and worrying and it’ll definitely put him to sleep. The downside is going into work tomorrow with a hangover and guaranteeing himself yet another terrible day.

He decides to mix the two options. For every two fingers of whiskey, he downs a glass of water. Throughout his marathon, he eats two bags of popcorn. Finally, when the third Indiana Jones movie has come to an end and his eyes won’t stay open, he takes a couple aspirin and shuffles to bed.

The next day isn’t so bad. He wakes up at 5:15 like every other morning. He takes more aspirin, showers, brushes his teeth, and skips breakfast. Just before he heads out the door, Castiel’s voice rings through his ears as if he were standing right behind Dean.

_I’d like you to take a personal day tomorrow._

A personal day. The only times Dean took personal days were to visit his mom over Thanksgiving and Christmas and that one time Sam got married. Other than that, he was at The Java 60 hours a week and spent his one day off worrying if he prepped enough donuts.

 _Fuck him,_ Dean thinks. _He doesn’t own me. He can’t tell me what to do._

He slams the door behind him and trucks off to work. When he arrives, he goes about his day as he normally would, trying not to think about the evening that had been planned out for him. Kate and Krissy show up half an hour after him and prep for the day in the lobby. Then, a little after nine in the morning, he hears the distinct sound of a power drill.

“What the fuck,” he mumbles to himself, irritated, wondering if this theme of weird fuckery is ever going to end.

Out in the front of the café, he finds three men gathered around the broken door, unscrewing the boards that Benny helped Dean attach to the frame. Upon closer inspection, one of the men is Benny himself.

Dean smiles when he catches his friend's attention. “What are you doing here, you son of a bitch?”

Benny returns his expression and offers a hand. Dean gives it a firm shake. “I’m here to fix your door, you cheapskate,” he drawls.

Dean feels embarrassed immediately. When Benny was over the other night, Dean explained that he couldn’t afford the new door at the moment. He was just lucky that it was summer and the awning out front kept the rain from coming in, and the few boards would be fine for a couple more weeks. “I thought we agreed on next month.”

“I know, you’re not paying for it.”

Dean’s brows scrunch together. He silently prays that Benny isn’t doing this out of the goodness of his heart because he’s not sure how he’ll ever repay him. “Who is?” It sounds more accusatory than he wanted.

Benny picks up a discarded clipboard and flips through the pages. “Some guy named Castiel Allen. Weird name. You know him?”

The name takes Dean aback. Castiel did this? He tucks the information of his identity away in his head and tries to look nonchalant as he shrugs. “Never heard of him before. Probably just one of those Good Samaritans who has too much money.”

Benny cracks a smile and muses, “Maybe so.”

Except that it’s not. Castiel paid for Benny to come fix his door after that redhead shot through it. Dean considers what it might mean, whether it was meant to be courteous or condescending. Or a bribe. Whether it was supposed to keep him quiet or push him toward showing up for that date, Dean wasn’t sure.

The rest of the café is empty, save for a person with their headphones on, looking at their laptop. He gestures with a thumb over his shoulder at the front counter. “You guys want something to eat or drink? On the house.”

The three of them order coffees. Dean whips them up, hands them out, and goes back into the kitchen to give them their space. A couple hours and plenty of noise later, Benny asks for Dean’s signature and takes him up on the offer for something to eat. Dean puts Krissy to work making sandwiches for all of them and they eat and shoot the shit before Benny sighs about his next appointment. The three men depart, and then it’s just Dean alone in his kitchen again.

Dean thought he made up his mind yesterday when he was handed that coffee sleeve that he wouldn’t be found within 500 feet of that guy ever again, if he had something to say about it. But Castiel having his door fixed hit a strange chord in Dean. It made him uncomfortable, unsure of what it actually meant, and he couldn’t shake the feeling for the rest of the day.

What could he actually want from Dean? He had no doubt that this date was either an excuse to get him somewhere to kill him or some kind of joke. Dean could show up to this place and be rejected because Castiel wasn’t there, while the guy sits back and laughs about how stupid and gullible Dean is. Or what if he is there? Somehow that idea is worse, because it made things more real.

What if the date goes badly and Castiel kills him? What if the date goes well and Castiel wants to see him again? What if it goes so well that Dean wants to see Castiel again?

Okay, that seems way too far fetched. Dean isn’t stupid enough to catch feelings for some well dressed criminal. It’s not like they’re going to fall in love and get married and go after people together with matching _his_ and _his_ hammers.

Right?

He shouldn’t even show up. He should go home, put on Netflix, and eat junk food. He should call his mom because it’s been too long since he’s talked to her and her voice would make him feel five times better. He should bake a batch of chocolate chip cookies, put his feet up on the coffee table, and keep himself out of harm’s way.

But, what if? What if Castiel really was just offering dinner and nothing else? What if he would hold true to his word and back off if Dean didn’t show any interest in him? What if he wasn’t as terrible as Dean thought he was? Yeah, sure, he held a hammer over Dean’s knees, but maybe he didn’t want to do it. Maybe he was just following orders. Maybe the threat was just a threat and he had no actual intentions of destroying Dean’s legs. Maybe he had gotten caught up in the wrong crowd and wanted out.

There are too many variables and questions and concerns. Dean forces himself to stop thinking about it and cleans the kitchen. He sweeps, scrubs, and mops the floor, then wipes down every surface he can find. Not only does he ignore Castiel’s instruction to skip work, but he stays late. 

At five, he finalizes his decision. He’ll go on this ‘date,’ but he’s bringing his pocket knife. It might not do a whole lot of good against a hammer (or a gun, if Castiel carries one), but there’s no way Dean is going to show up empty handed.

He drives home and takes another shower to wash away the smell of cleaning solution and fryer oil. He brushes his teeth again and puts on his only suit—the same one he wore to the bank when he asked for his loan and to Sam and Jess's wedding just six months prior. It’s a little stale after sitting in his closet untouched for so long, so he sprays on some Fabreze and then some cologne and calls it good. If he’d made up his damn mind sooner rather than later, he might have even gotten it dry cleaned. He tucks the thought away for next time.

Next time. Will there be a next time? Will there even be a _this time_?

_Shut up._

He leaves for the restaurant an entire 40 minutes early. It takes him half an hour to travel six miles in the Chicago traffic and he shows up in just enough time to find a parking space and have an attendant direct him toward the right elevator. When the doors open on his floor, he checks his watch and it’s exactly seven.

_Don’t be late._

He approaches the host at the podium inside. The man looks him up and down and Dean feels suddenly self conscious in his discount Men’s Warehouse suit. People who work and eat in a place like this probably have their suits hand made for them.

“Can I help you?”

“Dean. Uh, Winchester. I’m here to meet Castiel?”

The host runs a finger along the page of his book and finds whatever he’s looking for. He turns on his heel and says over his shoulder, “This way.”

The inside of the restaurant is way more incredible than what the pictures online showed him. He marvels at the art, both hanging and standing around the interior, and nearly trips over the first stair when the host leads him down into the dining room. They’re high up in a downtown building, on the 40-something-th floor, and Dean feels like he’s already losing money by just existing in this place.

Castiel is sitting at a table next to a window, looking at the blue skies. When he notices Dean and the host, he stands and smiles. He looks over Dean’s shoulder to the host. “Thank you, Conrad,” he says, dismissing him.

So, Castiel eats here often enough to be on a first-name basis with the host. Dean doesn’t know what to do with that information.

Castiel closes the distance between them and offers his hand to Dean, who takes it hesitantly. “I’m glad you made it, Dean.” He steps in even closer, plants a kiss on Dean’s cheek, and whispers into his ear, “Is that a knife in your pocket or are you just happy to see me?”

The back of Dean’s neck prickles. He thought he hid it well enough, but his slacks must be less forgiving than he believed.

Castiel backs away and motions to the chair opposite him. “Please, take a seat.”

Dean takes the chair Castiel offered and scoots in far enough to reach the table, but keeps enough room so that if he needs to make a break for it, he can. Outside of the window, Dean finds those blue skies Castiel was gazing at and makes out a dragon in the clouds. He doesn’t know what to say to the man.

“You worked today,” Castiel observes.

Dean’s ears burn. For the first time, he considers if there would be consequences for his actions. He also wonders how Castiel could tell. “Yeah.”

“I thought I told you to take a personal day.”

He sounds like Dean’s mother. _I thought I told you to do the dishes_ , she’d chide when she found Dean watching TV after school instead of doing his chores. “If I had, I would’ve just sat around all day and probably talked myself out of coming.”

Cas takes a moment to mull Dean’s words over and purses his lips. “Fair enough,” he concludes and picks up his menu to look it over. “Have you been here before? They have an excellent New York steak. You strike me as a man who appreciates a good steak.”

Of course he hasn’t been here before, what kind of question was that? Dean has to hold back the scowl that is threatening to cross his face. “What is this about?”

“This is about eating dinner,” Castiel answers, still looking at his menu.

“No, _this_.” Dean gestures between the two of them. “What is _this_ about?”

Castiel looks up at him. He folds his menu and sets it down on the table. “What do you expect me to say? I found myself attracted to you, so I asked you out for a date. Is that so abnormal?”

“It is when just the day before you almost broke my legs.”

Castiel looks down at the table. If Dean didn’t know any better, he’d say Castiel looked sad and guilty. But he remembers the way Castiel smiled with his mouth and not his eyes, the way he leaned in close and touched Dean's face like they were familiar with each other. His touch had felt cold and empty, more of a warning than a caress. And now here he is, pretending he was regretting his choices.

“Yes, I suppose you're right. I was hoping we could put that behind us.”

Dean is about to open his big mouth and say something that will probably get him killed when their waitress comes up. Castiel fluently orders two glasses of some foreign wine and the duck. When she turns to Dean, he flounders, not having looked at the menu even once. He orders the first thing that comes to mind.

“The New York steak. Medium rare.”

She smiles and takes off. Dean looks across the table at his ‘date,’ who is staring right back at him.

Did he actually mean he wanted to put it behind them or was he being facetious? His tone indicated the words were genuine, but did he actually expect Dean to just let something like that go? Had Castiel been thorough enough, Dean could have lost the ability to walk for the rest of his life, and Castiel wanted him to forget about it?

Dean feels anger boiling inside of him. Why did he even come here? To listen to this asshole shrug off his traumatizing B&E? To make Dean feel like the fear and distress he felt weren’t valid or important enough to bother addressing?

Under the table, Dean rubs a finger over the pocket knife. Maybe Castiel didn’t plan on killing him, but maybe Dean could plan on killing Castiel if he keeps this shit up.

Instead of exploding with all those people around them, Dean takes in a deep breath and bites his tongue. When he feels more in control, he says, “You had my door fixed.” And after a moment of consideration, he scowls, “Castiel _Allen_.”

Castiel levels him with a disapproving gaze. “Honestly, Dean, did you believe I would put my real name on that bill?”

Dean hadn’t considered that. He opens his mouth to retort, but nothing comes out. He stays silent.

Castiel continues, ignoring Dean’s stupor. “It was meant to be a sort of apology. I knew that it would take more than a few words and a hot meal to get myself into your good graces, and I understand that Benny Lafitte is a... _friend_ of yours.”

Castiel says friend like he knows about Dean’s history with Benny. He had been the first man Dean got involved with, the first one who solidified his attraction to men.

While Benny was helping Dean with some light construction inside the café right before it opened, they made a habit of staying late to drink beer and talk until one or both of them reluctantly called it a night. And one evening, when they were tipsy and chatty and getting a little more than friendly with their hands, Dean decided, _fuck it_ , and leaned in to kiss the guy.

They lasted about four months. Nothing bad happened, they just didn’t work out. Benny was still caught up on his ex and Dean spent more time panicking about how he would explain his bisexuality to his family than he did with his boyfriend.

After they broke things off, Dean didn’t see Benny for a little while. Six months later, Benny started coming in for coffee and talking to Dean about once a month, and before they knew it, they were back to hanging out again. Benny ended up marrying that ex, Andrea, and having a few rugrats.

Dean wonders how much of that Castiel already knows. Dean doesn’t go into detail about it. “He helped me out when I first started up The Java. We still get together sometimes.”

Castiel smiles, and Dean can tell from his expression that he knows everything Dean hasn’t said. How exactly did he learn about Benny? How did he have the time and resources to research about Dean’s non-publicized relationship from six years ago? How much else did he know?

The waitress shows back up to pour each of them a glass of wine. Dean is grateful for the break in tension between them, even if it only lasts a few moments. Castiel swirls, sniffs, and sips his wine and gives her a nod. Dean takes a drink of his wine as she wanders off and he grimaces. It’s dark red and dry. How much is he expected to drink to be considered polite? Does he even bother with such courtesies?

“You don’t like it,” Castiel comments.

“More of a cheap whiskey guy, myself.”

Castiel frowns at him. “We’ll have to work on refining your pallet, Dean Winchester.”

That sounds like a plan and a plan sounds like time and time sounds like Castiel actually wanted to get a real relationship out of this rather than just the date he invited Dean on. “How long is this supposed to go on for?”

Castiel shrugs. “As long as you’d like.”

“So, what, you want me to be your boyfriend or some shit?”

Castiel tilts his head. “I wouldn’t object to that.”

Fuck. He really did plan on keeping Dean around for a while. Dean leans into the table and lowers his voice. “I don’t want to be your fucking boyfriend, you sicko.”

Castiel is not phased with Dean’s attempt to intimidate him. “You don’t have to be. Like I said, if you aren’t interested, I’ll leave you alone. It’s that simple.”

Dean searches his face for some sort of tell and finds nothing but unwavering honesty. Maybe he really was telling the truth. So far, he was holding up everything he said to Dean, but there was no promise that the trend would continue.

“Good. I'm not interested.”

Castiel takes a long moment to regard him, long enough that Dean starts to squirm under his eyes. “Then why are you here?”

His words aren’t accusatory or impolite. They’re just curious.

It’s a question Dean wasn’t entirely ready to face head on. If he wanted to lie to himself, he’d chop it up to free food or an excuse to get out on a Friday night for the first time in years. But the honest side of Dean’s brain told him it had more to do with the prospect of excitement in his monotonous routine or the way Castiel was so devastatingly handsome or the way his heart fluttered when Castiel reached forward and pulled the marker from his apron—and it wasn’t because he thought Castiel would try to attack him again.

Maybe if they hadn’t met the way they did, Dean would have asked Castiel out first. There was no denying that Castiel was good looking and eloquent and exactly Dean’s type, give or take the horrifying look he had in his eyes when he wanted something.

“I could ask you the same thing,” Dean says. “Why did you ask me out? And don’t try to tell me about how pretty I am again.”

Castiel smiles, wide and sincere, and Dean feels a tug at his heart. “Well, I do think you’re pretty, but that’s not what I meant when I said I was attracted to you.”

“Then what did you mean?”

Castiel takes a pull at his wine and sets the glass down carefully, like he might break it. “I think you’re authentic and brave and witty. I think the devotion you have to the people in your life is unbreakable, even to a fault. I think you’re intelligent and quick on your feet and when you lie, it’s love that’s motivating you, not malice. You’re admirable. That’s why I find you attractive.”

Dean didn’t expect Castiel to already have so many thoughts and feelings about his personality, or any at all, really. The words swirl around in his head. He has no idea how to respond to such a commentary.

He decides to just ignore everything Castiel said. He doesn’t want to believe anything Castiel tells him, including compliments. His brain tells him this is all just a part of the elaborate scheme to get him alone and kill him.

“Are you gonna try to beat more information out of me?” he asks.

“Dean, we’re in a restaurant.”

“I don’t have any reason to believe that would stop you.”

Castiel sighs. “Despite what you might think of me, I do my best to keep up appearances in public. And I like to consider myself a gentleman. All intentions of beating information out of you ceased when I changed my mind and decided to take you out instead of take you _out_.”

That idea hits home. Sure, Dean understood that Castiel had planned on breaking some bones to get what he wanted, but maybe he wouldn’t have stopped there if Dean hadn’t lied to him. Maybe Dean would be dead right now instead of in a wheelchair if he weren’t so _quick on his feet_. He tries not to think about it.

Dean takes another gander at the restaurant they’re in, at the servers in button downs and slacks, at the wine glasses and dishes littering the other tables. “So, what exactly did you have planned for tonight?”

“Just dinner. I wouldn’t want to overwhelm you on our first date.”

“Is this how you usually treat a man?”

Castiel frowns. “I haven’t done this in a long time. With what I do for a living, I don’t have the opportunity to date often.”

“And what exactly is it that you do for a living?”

Castiel pauses like he’s contemplating telling Dean. Finally, he says, “I’m the personal assistant to the head of the Chicago Gospel.”

Dean’s eyes bug out of his head. The Gospel has been around for decades, right up there next to the Outfit, which was more or less quiet and retired. Dean heard their name come up on the news about once every month or two, whenever a body was found or some poor bastard went to the cops about being shaken down by a nondescript middle aged white guy. How many times had Castiel been that guy?

The Gospel used to be run by a man named Carver Edlund, but was taken over by his son Michael when Carver was found in a bathtub with a bullet in his head. It was ruled a suicide, even though no one believed it. His entire family had a alibi, even his wife, who completely lost her mind after he died.

“The _Gospel?”_

“Yes.”

“You—” Dean has to contain himself, feeling his emotions and voice rising. “So, you kill people? For a living?”

Castiel tilts his head this way and that, weighing the question. “More or less.”

Dean heaves in a deep breath. Okay, so his date is a mob boss assistant. Great. He runs a hand through his hair, wondering just how far in over his head he is.

“I can see how this may be considered a deal breaker,” Castiel acknowledges.

Dean barks out a single laugh. “You think? You’re a _murderer_.”

Castiel draws back like Dean had slapped him. He sets his jaw and Dean mentally prepares himself to be shot or stabbed right there in his chair.

“I cannot change what I am or what I’ve done,” Castiel says through forced composure. “I don’t kill without reason. I only take someone’s life if I truly believed the world would be a better place without them. And I can assure you that I may not be the safest person to be associated with, but I would never let anything happen to you. Even if you decided to leave right now, I would do everything in my power to guarantee your safety.”

Castiel’s eyes are no longer angry and hard. They've softened into something more like sadness.

Castiel might be dangerous and difficult to read, but so far, Dean had no proof that he was a liar. Dean could walk away right now and trust Castiel to keep his word. The idea sounds appealing, but not as enticing as sticking around to eat that steak and continue the bizarre angry flirting they were engaging in.

Dean nods. “Okay. I believe you.”

Castiel’s sad, pleading face slowly turns into a smile. “Good. Now, enough talk about the office.” He laces his fingers together, sets his elbows on the table, and drops his chin into the bridge of his hands. “Tell me more about Dean.”

— — —

The night goes way better than Dean ever thought it would. Not only does Castiel not murder him, but he holds a conversation like no other. Dean spends some time talking about himself, first vaguely, but then more in detail as Castiel asks him questions and requests elaboration.

Dean talks about all the studying he did before opening his café—from watching YouTube videos to working in a bakery to traveling to France for a few weeks. Castiel names all the countries he’s visited and Dean loses count somewhere in Africa. Dean explains his intense fear of planes and how he had to go to his doctor to beg for some Xanax for the his first flight at the grown-ass age of 25. Castiel laughs at him and tells him it wouldn’t be so bad if he were more used to it. Dean doesn’t want to get used to it, he wants to drive everywhere.

The two of them fall into a brief silence after dinner. While their food settles in their stomachs, they watch the sun set on the other side of the window. After a while, Castiel asks him if he had a favorite sunset.

Dean talks about the time, just after graduating high school, that he and Sam played Hey Mister outside a liquor store until someone bought them a six pack. They drove out to Clinton Lake and found a private spot to sit in the sand and drink their beer. They talked about how different things were going to be. At first, Sam jokingly complained about how he would have to pick up the chores Dean was leaving behind, but then his tone changed when he mentioned that he would miss those days they spent eating free burgers at the diner while their mom worked her shift.

When the sun set that night, the sky lit up in shades of purple and pink and orange. Sam, just 14 and drunk off of three beers, sniffled about how much he was going to miss his stupid big brother. Afterward, they laid down on the beach and watched the stars until it got cold and they went home.

When Dean turns away from the sunset in front of him to ask Castiel the same question, he finds the other man smiling softly at him.

He looks good like this, Dean admits to himself, when he's less formidable and more amicable.

Castiel explains that he saw his favorite sunset when he was staying in Hawaii the summer before his last year in college. He had been on the beach all day, trying and failing to surf, drinking martinis, and getting sunburnt. In the evening, the sun lowered to the horizon and the whole sky caught on fire.

When it’s dark out and the streets below them are illuminated by yellow and blue lights, Castiel orders two coffees and a slice of cheesecake. While they wait for their order to arrive, they briefly debate the age old argument: cake or pie? Castiel reasons that cheesecake is the perfect combination between the two and Dean disputes that cheesecake is neither cake _nor_ pie. Castiel decides it doesn’t matter which is better, because they don’t serve either at the restaurant.

Before Dean even thinks about it, he blurts out that next time they should go somewhere that has pie. His cheeks flush when he realizes what he’s said and snaps his mouth shut. Castiel smiles like he’s won some prize.

The coffee is so good, Dean is almost mad about it. Against himself, he closes his eyes and moans after his first sip. When he looks up, Castiel is staring at his lips. He points at his upper lip and Dean swipes at his face, finding a small mess of steamed milk there. He blushes.

He’s not sure exactly when he stopped fingering the bulge of his pocket knife through his pants for reassurance and started bashfully laughing at Castiel’s jokes, but he stops fighting it and just enjoys the night. Cas isn’t all that bad when he's smiling so big that his nose scrunches up and his eyes nearly crinkle close. He’s cute like that, when he looks happy.

When they finally finish, Castiel throws a few hundred dollar bills into the book the waitress gives him and he stands. Dean follows suit and together, they ride the elevator down to the parking garage.

On the way down, Dean feels his anxiety rise, suddenly worried again about how the evening would end. Would Castiel finally stab him when they were alone and in the dark? Would he push Dean up against a car and stick his tongue down his throat? Would he tell Dean when and where to meet him for their second date? Did he want a second date? Did _Dean_ want a second date?

Dean isn’t sure if he’s supposed to follow Cas or if Cas is following him, but when he silently heads for the Impala, Cas is right there beside him. When they get to the car, Dean pulls out his keys and fiddles with them.

 _God,_ he thinks _. I’m acting like some teenage girl._

“Thanks,” he says, the first words spoken since Castiel asked if he was ready to leave. “For dinner. And also not killing me.”

Cas smiles and doesn’t say anything. He steps in closer and Dean breathes in his cologne. His heart skips a beat when Castiel presses his lips gently to Dean’s cheek before stepping away. “Have a good night, Dean. I hope to see you again.”

Unceremoniously, Castiel turns around and paces off to the other side of the garage. Dean stand there like an idiot and watches him walk away, guiltlessly checking him out and simultaneously wondering how he managed to end up in whatever position he was currently in.


	4. Chapter 4

**Notes for the Chapter:**

> I meant to post this last night, but had a family emergency to tend to. So, here it is tonight! :D

It doesn’t matter what he does, Dean can’t stop thinking about Castiel.

It’s not that he means to. Sometimes Castiel pops up in his head while he’s frying donuts. Sometimes Dean will replay things that Cas said while he’s driving to and from work. Sometimes his smile just appears in Dean’s head and Dean finds himself smiling too. After a few days, Dean barely even notices it until it’s too late; Castiel will creep into his mind and just sit there for an hour or two before Dean realizes he’s there.

It’s maddening. Castiel was never supposed to turn into a guy Dean was actually interested in—and he’s not. Dean’s not interested in Castiel. How could he be?

Except that he is. He can’t help the way his brain conjures up fantasies of going on another date. He thinks about how good Cas looked the other night—dressed up in a suit and tie, just like the other two times they’d met, but for some reason it was different the night they went out. Dean can’t put his finger on what it was about him. Not to mention the scent of his cologne when he pressed up close to Dean. Dean floods with heat whenever he remembers that smell.

Four days after the date, Dean went to bed and dreamt about him. Castiel tied him to a chair with tight knots and stood before him with dark eyes. He fisted a hand in Dean's hair and just when Dean thought he was going to be hit, Castiel leaned in and kissed him hard. He woke up a moment later, sweaty and aroused, but fought the urge to reach down into his boxers. He took a cold shower instead.

This was never supposed to happen. Castiel is a terrible, scary person. He admitted to killing people before. He admitted that he almost killed  _Dean_. He’s one of the top ranking members of a freaking  mafia and BFFs with Michael Edlund. He’s probably still after Charlie, and who knows? Maybe he’s still after Dean. Maybe he just likes to play with his food before he kills it.

But he’s also smart and charming and generous. Dean couldn’t stop the blush that would sneak up onto his cheeks when he thought about all the good things Cas had to say about him. He didn’t know whether to believe them or not, but even if they were lies, they were still flattering.

He almost felt guilty for not fully trusting him. On one hand, who would trust a guy like that, who assaulted and wounded and killed people before? Someone who almost did all three of those things to Dean just over a week ago? But he didn’t have any reason not to believe every word Castiel said. He had plenty of opportunities to lie. He didn’t have to tell Dean he was Michael’s assistant or confess to being a murderer or even talk about himself and his travels. He chose to.

Dean thinks his character is more impacted by honesty than brutal actions. At least he had been honest while he was threatening Dean. He grants that he’d rather have someone with an affinity for hammers than one for lying.

It’s a Sunday, the second day of August, when he leaves work and steps into the sunshine of a beautiful afternoon only to stop in his tracks at the edge of the café’s small parking lot. Castiel is there, leaning against the Impala like he owns it. His arms are crossed, sunglasses on, and his head is turned to the right. Dean wonders what he’s looking at.

Dean kicks himself for thinking about it, but he looks so fucking  _good_. His hair is a little tousled and he’s dressed like a normal person instead of a tax accountant. He’s donned in just a Led Zepplin t-shirt and fitted jeans. Dean questions if it’s really even him.

Dean approaches cautiously. Would this be it? The final nail in the coffin he built for himself? But then Cas turns to look at him and smiles wide, and all of Dean’s worries melt away.

How did he have the power to do that? Just rid Dean of his worries with a single facial expression, without even saying anything, without even being in reaching distance?

A small part of Dean knows exactly why, but he doesn’t think it.

He stops a few feet away from Cas, brows drawn together. Cas just looks behind him at the car, then back at Dean.

“This sure is a beautiful car, Dean Winchester. Where did you get it?”

The question takes him aback. He came all the way over, after Dean told him he wasn’t interested, to talk about his ride? Dean had been sure in the statement he made just over a week ago, but after spending so much time with Cas in his head, he’s starting to doubt his own opinion. “It was my dad’s.”

Castiel gazes at Dean a beat longer, probably waiting for him to elaborate. When Dean doesn’t, Castiel shrugs and takes off his glasses, hooks them onto the collar of his shirt. “I like it. I meant to ask you about it last week, but I was sort of caught up with something even more good looking.”

Castiel winks at him. Dean just stares, and wonders aloud, “What the hell are you doing here?”

“I thought we could go for a drive.” Castiel pushes off the side of the car and rounds to the other side, no doubt expecting Dean to just go along with whatever rendezvous he had planned for them.

Dean doesn’t move to unlock the car. He wants to trust Cas, because he hasn’t lied to him yet (that Dean knows of), but it’s hard when Dean knows what he’s capable of. He could tell Dean to drive them to some sort of secondary location to off him and throw his body in a river.

Cas lays both hands on the top of the car. “What, Dean? Even after our more than pleasant evening together, do you still believe that I have bad intentions?”

_Absolutely_ , Dean thinks. Then, he tacks on, _Maybe_. “Where are we going?”

“To the park.”

“Why?”

“For a date.”

“Who said I don’t already have plans?”

Castiel cocks an eyebrow. “You? Have plans?”

What an asshole. No, Dean didn’t have plans, but  _still_. He scowls. “I could have plans.”

“You could, but you don’t. Now, come on, it’s a beautiful day, I’m craving a cheeseburger, and I want to spend time with you.” Cas gives his best puppy face.

Dean’s not sure how to argue with that because, damn, Castiel noticed it was nice out and decided he wanted to enjoy it with Dean. He couldn’t lie and say that his stomach didn’t do a little flip.

He unlocks the car and they both climb in. Cas has a smug smile on his stupid face.

Castiel directs Dean to a a ramp in the middle of the street just west of Maggie Daley Park. He scowls at the sight of the underground parking garage, worried about putting his baby in a spot surrounded by bad drivers, but he knows he won’t be able to find any better parking in the middle of Chicago on a Sunday afternoon. When they pull in, Cas hands his phone over to Dean with a QR code on the screen.

“What the hell is this?” Dean asks.

“I reserved a spot for us. I wanted to make sure that we would have parking once we got here.”

“That’s a thing? Reserving parking in a ramp?”

Cas leans over the bench toward Dean. “Everything’s a thing, Dean.”

There’s that cologne again. Warm and musky and a bit like honey. Dean gets the sudden urge to pull Cas into his arms and bury his face in his neck. Instead, he leans out the window, away from Castiel, and scans the phone at the terminal.

They find a spot on the second level and Dean backs her in. He tucks the mirrors against the car for good measure and promises her he’ll be right back.

Cas leads the way up the stairs to where they’re deposited onto Monroe Street. It’s only a five minute walk to the corner of the park and when they step onto the walkway, Dean turns to look at Cas for the first time since they were in the car.

The sun is bright and hot, but Castiel is arguably hotter. Even with his eyes covered up by those shades again, he looks great in the minimal clothing he’s wearing. Dean hadn’t realized before that Cas was hiding lean but prominent muscles and a slim waist under those suit jackets. His fingers itch to reach out and touch him.

Half of his brain is asking,  _What the fuck are you thinking_ , and the other half is asking,  _What’s stopping you? He’s interested, why can’t you be?_

They find the Rink Café up by the skating ribbon. Castiel orders himself a cheeseburger, bag of chips, and a fountain drink. Dean tells the attendant to make it two of everything. When they get their orders in hand, they find an empty picnic table to sit at and dig in.

Castiel is devouring his burger like he hasn’t eaten in a week, just absolutely demolishing the thing. It drips mustard down into the basket, narrowly missing his t-shirt.

“Eat much?” Dean comments.

Cas just smiles down at his sandwich. “These make me very happy.”

Dean rolls his eyes in an attempt to hide his smirk, but he’s sure it doest help in even the slightest. Castiel ends up with a smudge of ketchup on the corner of his mouth and all Dean can think about is how stupidly adorable he is.

“How was your day?” Cas asks around a bite.

Dean shrugs. “Just like all the others, I guess.”

“Oh, come on. Nothing exciting happened today?”

Dean thinks back on his shift. Kate’s boyfriend and his best friend came in with cameras and teased her for a solid half hour about how she was working too much and wasn’t getting in front of the camera enough for their movie. Ronald tried to convince Dean that the Coronvirus was a hoax created by the government to distract us from the primary election. For some reason, he doesn’t want to tell Cas about any of this.

“One of my bagels came out looking like a butt,” he says instead.

Cas giggles. “Was it a good butt?”

“I think the kids these days are calling it  _thick_."

Cas bellows out a completely uncontrolled laugh. His head is thrown back and Dean watches him shake under his fit of excitement. Dean tries not to think about how the sound is something he wouldn’t mind listening to for days on end.

“That’s the funniest thing I’ve heard all week,” Cas says once he’s calmed down.

Dean hadn’t thought it was entirely all that funny, but one side of his mouth quirks up. “Not too many comedians in the office, I take it?”

Castiel shakes his head. “Uriel has the best sense of humor of us all, but it’s a little dry for my taste. He was there with me the night we met.”

“ _That_ guy?” Dean thinks back on that big guy picked him up and threw him onto the counter like he was just a sack of potatoes. The way he took a punch to the jaw and barely noticed it. “ _He’s_ the funniest in the office?”

“Believe it or not.”

He doesn’t, but maybe if Uriel turned out to be as cool as Cas when he wasn’t shaking someone down, Dean might toy with the idea a little more. “Yeah, well. How was your day?”

Cas hums as he chews a pretty large bite of that burger. “Last week found a virus that’s been causing a disturbance in the network. We’re not sure how to get rid of it yet, but we’re monitoring it. Today I spent some time looking into it.”

Dean only has half an idea of what that analogy means, but doesn’t question it. Not in public, anyway. “What kind of disturbance?”

“It’s leaking private information to another network we don’t wish to be associated with. One that has intentions of bring our network down."

Oh. While Dean had sort of come to terms with Cas being a killer, he hadn’t thought about the Gospel having enemies that could possibly pose a threat to the guy he was kinda starting to like.

Oh god, was he starting to _like_ Cas? He could accept that he was attracted to the guy, but to actually _like_ him?

No. Fuck no.  _ Stop that._

He shoves a few fries into his mouth and chews slowly to stop himself from saying something that he’s not even sure about yet. “You’ll take care of it, right?”

“We always do.” Cas smiles, and goddammit, he looks so happy and relaxed, Dean could almost believe he was just a regular guy and they were just on a regular date.

They eat in silence after that, just for a few more minutes until they finish up. They listen to the white noise of conversations and squealing children and traffic around them. Once their baskets are empty, they dump their trash into a can, and Cas runs back to the café. He comes back with two large ice cream cones and offers one to Dean.

They walk down to the south side of Maggie Daley, through Butler Field, and end up at the fountain by the time their ice cream cones are finished. Dean's been to this park before, but it always ended up being cloudy or windy or with the wrong person, but this time it’s all blue skies and 80° weather and a handsome man by his side.

Cas asks Dean more about his brother. Dean ends up talking about Sam for a solid twenty minutes, going on and on about how proud he was when Sam got into Stanford and then into law school and then into a firm. He talks about how beautiful Sam and Jess’s wedding was and the outrageous bachelor party they had the day before and the grill he spent way too much money on for their wedding present.

By the end of his speech, Cas squeezes his hand, and Dean can’t remember when they latched onto each other. He tries to casually slip his hand from Cas's and run his fingers through his hair, but he’s sure he's about as transparent as a cup of water.

Luckily, Cas doesn’t comment on it. The two of them chuck a handful of pennies into the fountain. He’s not sure about Cas, but Dean isn’t making any wishes.

On their way back to Maggie Daley, Cas asks him, out of nowhere, “Why did you give us the address that you did?”

Dean hesitates, wondering if Cas had some sort of hidden agenda behind the question. What would he do if he didn’t like Dean’s answer? “I used to live there with a buddy of mine. It was the first thing that popped into my head.”

He chances a glance at Cas, who is smiling softly.

“Well, I’m glad you thought of it. Not only did it save your legs, it also gave me the excuse to come see you again.”

“What was your excuse this time?”

Cas looks up at the sky, that happy, content expression still present on his face. “Sunshine, the smell of freshly cut grass, and cheeseburgers. These are a few of my favorite simple pleasures and I wanted to share them with you.”

“So, what, you saw it was nice out and figured you'd drag me out here for burgers and ice cream?”

Cas beams at him. “Yes, exactly.” He leans over and bumps his shoulder into Dean’s. “And I didn’t have a very good day at work. I knew seeing you would cheer me up.”

Dean’s cheeks heat up. His suspicions were true, Cas actually thought about him and showed up just to spend time together.

Dean can’t remember the last time someone acted like this with him. Sure he’d had his fair share of girlfriends (and the one boyfriend), first dates, and one night stands, but he hasn’t had someone around in a long time who just randomly decided that they wanted to see him and actually did it. After one date. Usually there’s the first date and maybe he calls whoever it was a few days later for a second meet up, but Dean’s always the one making the call. He’s never been on the receiving end of someone making the next move and sure as hell never had anyone just show up and take him out.

The fact that Castiel is already showing more interest in him than about a decade and a half of other partners said something. It makes him feel something. He’s not entirely sure what; maybe appreciated or important. And  Cas gave that to him. Even during the year he spent with Lisa, the longest relationship of his 31 years on this earth, he never felt as wanted.

“You really have something out for me, huh?”

“I thought I made that obvious.”

Yeah, he did. Dean is just having a hard time believing it. Years of his own self doubt ingrained into his head that he wasn’t worth anyone’s time. That’s why he and Lisa didn’t work out, or any of his relationships, really.

_ Maybe this time could be different,  _ he thinks.

 _It’s already different,_ he argues with himself, _because the others weren’t in the freaking mafia._

Castiel sighs next to him. “I know I said it’s a nice day, and it is, it’s just so  _hot_.” He turns to Dean. “Do you have air conditioning at your place?”

Oh, jeez. Dean was just starting to wrap his head around enjoying the time he and Cas were spending together, but the reality that Cas was dangerous and would one day want to go back to Dean’s apartment knocked him out of his stupor. “Yeah. But, uh... I’m still a little on the fence about you still, and I’m not sure I want you knowing where I live.”

Dean braces for anger or passive aggressiveness, for a flippant comment that it didn’t matter if Castiel knew where he lived or not because he could murder him anywhere. But Cas just raises an unimpressed eyebrow at him. “Dean, I already know where you live. I also know that you have air conditioning, I was just trying to be modest.”

Oh. Great. So Cas knew where Dean slept. That's a  comforting thought.

But... Cas knew where he slept. And he hadn’t taken the opportunity to kill him yet. Of all the times Dean was peacefully knocked out cold in the middle of the night, all the chances Cas had to slip in and slit his throat and leave him for dead, he never did.

There are no more logical reasons Dean has to hold grudges again Cas now. Sure, he could be mad about the whole breaking and entering thing last month, but Cas is here, proving himself, doing his best to show that he isn’t the scumbag Dean had him pegged for. He’s putting in effort, and that’s a lot more than most of Dean’s previous partners had ever done.

This is the exact moment that Dean Winchester makes the critical decision that Castiel could actually be trusted. After fiddling with the concept for the past two weeks since they met, nothing solidified the idea more.

So Dean smiles, and says, “Okay. My place it is.”

He peers at Cas from the side and sees his face light up.

The two of them meander back to the underground parking garage and climb inside his baby—still intact and not a scratch on her, thank god. It’s only a fifteen minute drive back home, and they spend the time with the windows rolled down and classic rock blaring from the radio.

Cas sticks his arm out into the wind and sings along to Foreigner and The Allman Brothers Band and Foghat when they each come on. Dean’s a little surprised with his taste in music—he half expected Castiel to be the kind of guy to listen to lounge music or some crap.

When they get back to his apartment, Dean lets them in the front door and immediately goes to the thermostat to turn on the air.

And stops.

“Hey, Cas?”

“Yes, Dean?”

He flicks the air on and turns to find Castiel leaning up against the kitchen counter. He looks so casual and at home in Dean’s apartment. “I have central air.”

Castiel’s eyes shift a little, surely confused. “Yes, you do.”

“I don’t have a window unit.”

Cas frowns and nods. “That’s true as far as I know.”

Dean crosses his arms. “So, how did you know I had air conditioning if you can’t see abox in the window?”

Castiel’s shrug is all too offhanded. “I let myself inside once.”

“You—” Dean sets his jaw and takes a deep breath through his nose. “You broke into my apartment?”

Cas bites his lip. He looks like he’s just now considering that wasn’t the best of ideas. “I picked the lock while you were at work one day.”

“ _Why?_ ”

Cas takes a few steps closer to Dean, stopping just short of being toe to toe. He opens his mouth. Closes it. Looks down. “I had to make sure you weren’t a part of the virus.”

Dean takes that information and realizes that maybe Cas didn’t trust Dean as much as Dean trusted Cas. And, man, did that feel like a slap in the face.

“You could’ve talked to me about it.”

“You could’ve lied about it.” Cas finally looks up at him. He looks so small like this. Dean never thought he could’ve looked so vulnerable when he could effortlessly put the fear of god into someone’s heart. “I’m sorry, Dean. It won’t happen again.”

Dean believes him. How could he not?

He sighs. “Don’t make me put cameras in here.”

Cas appears to unwind a little and dares a smile. “Cas, huh?”

Dean took a moment too long to remember letting the nickname slip without asking him if he liked it or not first. “As long as that’s alright?”

Cas smile brightens and he nods.

Dean moves around him and opens the fridge. He pulls out two beers, opens each of them, and hands one to Cas. “Tell me more about this virus.”

They settle onto opposite sides of the couch. Cas tells him about the Chicago Omens—an up and coming mafia that emerged on their radar a few months back, but they didn’t pay any attention to them at the time. Now, one of Michael’s brothers is communicating with them.

Cas explains that Carver Edlund had four sons: Michael, Lucas, Gabriel, and Raphael. Raphael was the product of an affaire Carver had on his wife, and was denied any sort of chance to take over when their father died. Gabriel didn’t want anything to do with it, but Michael and Lucas fought with words and fists over who would take the seat at the head of the table. It wasn’t long before an ‘anonymous tip’ lead to Lucas’s arrest and Michael became the new boss.

“So, now Raphael is pissed that he was never considered an option and he’s conversing with the Omens.” Cas pops the top on his second beer. “We have reason to believe he’s attempting to arrange an assassination.”

“On Michael.”

Cas nods. “But we have no doubt that he’ll take down anyone else in his way. I actually have the theory that Raphael would likely try to start anew and hire a whole new team rather than fight for the respect of Michael’s loyalists.”

Dean picks at the label of his bottle, almost empty. “So, this guy’s a real threat, huh? Sounds kinda scary.”

“It is and it isn’t. We know that Raphael is working with them, and we know what his plans are. We’ve been supervising him, but he doesn’t know that we know. We’ve been keeping him  just out of the loop enough so he doesn’t have every bit of information to give to the Omens. I’m just worried about Michael more than anything."

Dean feels a soft pang of jealousy. “You really like the guy.”

Cas looks over Dean’s shoulder distantly instead of keeping his gaze. “Michael and I grew up together. I moved to Chicago when I was twelve and he became my best friend on the first day. We’ve been inseparable ever since.”

Dean nods. “So, does this mean I have competition?” It’s light and teasing, just an effort to get Cas to loosen up and stop stressing.

It works. Cas rolls his eyes. “Against a married straight man? Yes, you have competition.” He smiles at Dean. “But enough talk about the office. Tell me something I don’t know about you yet.”

Dean chuckles, but ends up telling Cas about his fear of snakes. After that, he talks about his dad, who died when he was eleven. Then he explains that he had a pet up until recent—a homeless tabby he found on the street after graduating college who lived with him up until about a year ago when she passed. He lists off his favorite songs and tells elaborate stories of his best memories associated with them.

Cas quietly listens, content with just leaning against the back of the couch, legs tucked under him, chin resting on his fist. Sometimes he interjects with laughter or comments or questions, but overall, he just focuses on Dean while he talks. Like he actually cared about what Dean had to say.

When he runs out of things to tell Cas, he suggests a movie. Cas smiles and asks him if he has  _The Breakfast Club_.

Through the movie, the two of them spend more time talking, mostly about their own high school experiences. Cas, as it turns out, was one of those really athletic, but not jocky nerds. Straight A’s, almost valedictorian, running cross country every fall and track every spring. He was on the debate team and in the marching band—percussion, of course.

When Cas tells him about his band days, Dean ends up laughing a little too much and Castiel decides to turn the attention around on him. Dean just tells Cas that he got good enough grades, wrestled and played baseball, and was a real lady’s man, but that was about all there was to him. Cas doesn’t look like he believes him, but instead of asking more questions, he just sinks a little further into the couch and watches the movie again.

When it finally finishes, it’s just past nine pm and Dean almost doesn’t believe the clock on the wall when he checks the time. He spent a solid five hours with Cas today and hadn’t even realized the time go by. He remembers their last date, an entire hour and a half affair that made Dean feel every second that ticked by.

Dean just about opens his mouth to ask if Cas wants to put on another movie, but the other man glances at his watch and sighs. “I should probably get going,” he reasons.

_What?_ Dean wants to ask. But, oh, right, this date would likely not end up like most of his other second dates. It’s hard to remember that Cas isn’t like the other people he’s dated in the past.

Not that he expected Cas to stick around and put out or anything, but throughout the movie, Dean wondered how nice it would be to hold his hand or sit close enough that their legs touched or possibly even indulge in a light make out session. Because, yeah, Dean was definitely thinking about kissing the guy when ‘Don’t You’ came on at the end.

“Right,” Dean agrees reluctantly. “Yeah, okay.”

They stand at the same time and awkwardly shift over to the front door. Dean thinks about asking him to stay, decides against it. He opens the door and watches Cas pat himself down for his phone and wallet, and then he directs a smile at Dean.

“I had a good day today. Thank you.”

Dean bites his lip and debates saying what’s on his mind. That being, what made him so special? What made him the guy Cas decided to spend time with after a bad day at ‘work’? What set him apart from everyone else?

His words come out as, “Why are you doing this? With me?”

Cas tilts his head. “I thought I explained this before.”

Dean wrings his hands together, looking down at his socked feet in front of Castiel’s shoe clad ones. “Yeah, but, there’s a ton of guys in Chicago who are devoted and quick on their feet. Why me?”

He feels more than sees Cas lean in and he takes the opportunity to breathe in his scent. Basks in it a little. Cas’s mouth connects with his cheek again before he draws back. For some reason, despite how brave Cas thought Dean was last week, he just can’t look up and meet his eyes.

“I like you, Dean. I hope that one day, you’ll like me too.”

He walks out the door Dean is holding and doesn't look back. Dean feels the regret creeping into him for not getting one last look at Cas's face before he left.


	5. Chapter 5

**Notes for the Chapter:**

> **Warning: mentions of torture, pedophelie/molestation, and on screen killing.**

Castiel twirls the knife in his hand as he stares down at the man in front of him. He wonders how long he should keep up this torment—they’d started about ten minutes ago, mostly with taunting and not-too-deep cuts here and there. They’re all incredibly unkept; Castiel, the man before him, and Gabriel are covered in dirt, sweat, and blood, and the air around them is thick with hostility and tastes like copper.

Most of the filth on Castiel and Gabriel originated from the first perp of the night: the owner of a sketchy pawn shop on the outskirts of town who sold videos of little girls. They hashed and slashed through him for a solid forty minutes before he gave up the names of his two cinematographers. With the information, Castiel put a bullet in his chest and left him to bleed out in his own store.

They found the first cameraman walking to his car from his apartment. At that point, Castiel was boiling over with rage, having spent the past half a month researching and tracking, had bled a man out, and spent the entire time being forced to think about what they did for pleasure and money. Something took over in him and Castiel tackled the guy to the ground. Gabriel let him throw punches until he wore himself out, then stepped in close and shot him.

The second one is tied up just a foot away now. If Castiel didn’t get out all his anger with the former, he’s sure it’ll be gone with the latter. Besides, this asshole only deserved to suffer.

He uses the knife to tilt up the man’s face. It earns him a sneer.

“You’re messing with the wrong fucking guy,” he spits.

Just behind him, Gabriel clicks his tongue. “Big words coming from someone tied up and already half dead,” he says.

“ _Fuck_ you. You think you’re so big and bad? I’ll make your life a living fucking hell.”

Castiel sighs. As much fun as it is poking knives into pedophiles, he’s tired and has other ideas on how to spend his night. Ideas that include a handsome baker and an obscene amount of cuddling.

He squats in front of him and drags the back of the knife down the side of the man’s face, across his jaw, and down to the side of his neck. “No,” Castiel disagrees, “you won't.”

With a single, quick movement, he slits the man’s throat, spraying blood across Castiel’s chin and coat. He gasps and gargles on the blood for several seconds until his body goes limp and his eyes are blank.

 _Finally,_ Castiel thinks. It took him almost two weeks to get here, but the three sick fucks running their own home movie business are finally dead, each of them coming to the painful and violent end that they were meant to have.

He stands up straight again and wipes the knife on his coat. It’s absolutely ruined. He supposes it’s about time for a new one, anyway; trench coats are probably too 1960’s, but it’s his favorite and he feels a tug at his heart knowing it’ll be in the garbage by the end of the night.

“I say,” Gabriel suggests, “that we check the place and get the hell out of here.”

Sounds like the usual. With each hit, they find the evidence (both their own and the victim’s) to either display or get rid of. They go through the checklist. Fingerprints were avoided with gloves. Shoes will be thrown away. Any security footage will be reviewed by their tech. Castiel will clean off the knife and put it right back in the block on the kitchen counter. They’ll untie the man and toss the rope in a dumpster on the way home.

They discover about a dozen DVD videos in a closet and drop them at the dead man’s feet. Gabriel unties him as Castiel rinses and replaces the knife. When everything looks back to normal—save for the body and puddle of blood—Gabriel sighs.

“I’m feeling Chinese food. Wanna join me?”

Castiel’s face twists up in disinterest. Even though all three men they killed tonight were terrible, disgusting wastes of space, he still has a foul mood and no appetite. It doesn’t matter if his deeds were more good than bad, nothing kept him from deflating after a kill. Gabriel, on the other hand, usually had food on his mind.

He shakes his head. “I think I’ll just be going home.”

Gabriel shrugs. “Suit yourself. You need a ride home?”

“No, thank you. Enjoy your night.”

Gabriel waves and is already on the phone, ordering sweet and sour chicken with rice before he’s even out the front door. Castiel watches him leave, and once he’s alone again, he takes a moment to relax.

It’s been a long night. If he’s really being honest with himself, it’s been a long two weeks. Not only had he been working endlessly to get to where he is now, he also had his other responsibilities to take care of. He showed up to mass with Michael; visited Mrs. Edlund in the hospital for hours as she tried to remember him, recalled, and then promptly forgot again; attended their usual thrice weekly meetings; visited social clubs to drink and puff cigars until the sun came up; and made appearances at a few of the local businesses Michael owned.

While Castiel’s job is rewarding and beneficial, he’d rather not follow Michael around for 50 hours a week briefing the other members, collecting payments, and running errands like a common intern.

Sometimes, he wonders if he never should have accepted the position. Michael helped him get into his dream college and paid for his tuition after Castiel became his assistant, but he could have gotten into his field of study and lived a normal life. Sure, accounting would have been boring and monotonous, but at least he wouldn’t be a murderer. Regardless of how bad the people he killed were, he’d rather not have multiple kills under his belt.

Maybe he would have a comfortable job in an office. Maybe he would live in a house in the suburbs and not a high-rise downtown apartment. Maybe he would have a cat and a garden and a hobby. Maybe he would be in a stable relationship with someone who loved him.

He has Dean. Sort of. He’s still not sure if it’s fear or attraction that keeps him from running away when he sees Castiel. He’s not sure how long he’ll last before he realizes that Castiel is someone he shouldn’t be around and finally tell him to fuck off.

But a man can dream, can’t he? He believes so, and he definitely dreams. He dreams of late nights filled with quiet pants and soft whimpers. He dreams of Monday mornings with croissants and coffee and warm blankets. He dreams of the day Dean leans in to kiss him for the first time.

He hasn’t seen Dean since he started his investigation on the pawn shop owner. Their last date at the park had been pleasant and fulfilling, but left much to be desired. Dean kept his distance the entire afternoon, only breaking his resolve to grasp Castiel’s hand while excitably talking about his little brother. He must not have realized it, because when he looked down at their hands, he pulled away.

Hopefully, he’ll one day sit a little closer and they can touch like people do. He doesn't know how long it will take before Dean comes around to Castiel—or if he ever will.

Before he knows it, he’s pulling out his phone and dialing a taxi. He gives them an address a few blocks away from the dead man's house and begins his short commute in the chilly late evening air.

He should go back to his apartment. He should throw away his shoes, give up his favorite coat, and shower. He should crawl into that bed of his that's too big for one person and fall asleep. He should not be worrying about whether or not a man likes him back.

So why can’t he stop thinking about Dean? Seeing him sounds like a much better idea than going back to Castiel’s cold, empty apartment. Maybe they’ll even sit around and talk about sunsets like they did on their first date, or find another movie to ignore while they chat about the good ol’ days like last time.

A yellow cab pulls up to Castiel. He climbs inside and is prepared to give out his home address while he tells the driver to take him to Damen and Dickens in Bucktown. The driver barely glances at him in the rearview mirror and doesn’t say anything about Castiel’s bloody attire; just drives off and taps the steering wheel to the rhythm of the music playing from the radio. Castiel silently thanks him for not attempting to make small talk.

They arrive at Dean’s corner nearly twenty minutes later. Castiel hands the man a few twenties before getting out. The cab is gone in a matter of seconds.

Dean lives just above a little antique store in a black and white building. Inside, his small kitchen has deep brown cabinets and a dainty dining table for two. The cozy living room is decorated much like his café and hosts a small sofa chaise and a recliner. The bedroom is donned in shades of brown and green like he was trying to bring the forest to Chicago.

The first time Castiel had been to Dean’s apartment, he was surprised with how much character it had. There are house plants and candles and books and photos everywhere. He has basil, chives, and parsley growing in his kitchen window. All around, Castiel found nicknacks and treasures from who-knows-where that Dean decided to keep. He even has medals and trophies from his time as a wrestler and baseball player.

The paintings that decorate his walls are from local artists, not IKEA. Every framed photo shows Dean’s family or friends, sometimes with him with them. His furniture is worn, but loved and taken care of. He has a collection of mugs from different places he’s visited. Almost nothing came in a set, but somehow everything matches in the way Dean put it together.

It’s obvious that Dean put a lot of thought and effort into his home. Castiel never had the knack for interior design. His own apartment is all stainless steel appliances and white walls and minimal decor. He doesn’t know how to turn a house into a home the way Dean does.

Castiel lets himself into the building with a few wiggles of the door handle. The lock must have broken a while ago because it gives easily. He’s up the stairs and down the hall before too long, standing in front of the last unit on the right.

He checks his watch. It’s just after 11 pm. Tomorrow is Monday, Dean’s usual one day off, so he’ll likely be awake, but probably getting ready for bed or enjoying his time off. Castiel wonders what he’s up to when he’s not at work. Does he have interests outside of donuts and coffee?

 _What are you thinking?_ he asks himself. _You’re going to intrude on him on the one night he gives himself to stay up late and demand his attention when he should be relaxing?_

It all sounds so selfish. He shouldn’t be here; he should let Dean rest and come back tomorrow. Or maybe never again. He should just leave Dean alone to live his life peacefully the way he was meant to.

Castiel never had any right to walk into Dean’s life the way he did. He should have stuck to the plan: get Charlie’s home address and leave him be. When Dean gave him his own old address, Castiel should have made good on his promise, broken a knee or two, and left him. He didn’t know where the nerve came from to proposition Dean for a date, or to show up to take him out to the park.

He didn’t know where he went so wrong tonight that he’s standing just a few yards from an unsuspecting Dean. How he got here is a mystery to him. A good man would turn back and disappear. A better man wouldn’t be here in the first place.

All of this should stop him from knocking, but he still raises his hand and raps his knuckles against the wood of the door. Anxiety swirls in his gut while he waits for the answer.

_This is stupid. I'm covered in a dead man’s blood, smell like a dirt road, and I’ve been awake since 5 am. I’m the sore eyes, not the sight._

Dean opens the door. His eyes widen when he takes in Castiel.

This is a mistake. It’s time to give up and leave. If Dean wasn’t terrified of him before, he sure must be now. Castiel feels the need to sprint back down the hall and run all the way home, but something is grounding him. He can't move. His hands shake.

“ _Cas?_ ”

“Hello, Dean.” He’s surprised his voice doesn’t quiver.

Dean stares for another long moment, probably trying to find the words to tell him to go away and never come back. Probably realizing just how real this whole mobster thing actually is. Probably scared for his own life.

This is the reality of living a life in the mafia. It’s blood and gore. It’s shake downs and murder. It’s bruised hands and alibis and running. It’s showing up at the someone’s door at nearly midnight because the possibility of ruining the one good thing in Castiel’s life is somehow better than being alone.

Castiel shouldn’t be putting Dean in this situation. Just being here made Dean an accessory to three murders. He told himself that he would keep Dean at arm’s length from the dangerous side of his life, yet here he is, like an idiot. He never should have come here. The last time he let something like this happen, someone he loved died.

_Keeping him at a distance from your job didn’t help him at all, why would it help Dean?_

He’s about to open his mouth to apologize and say goodbye when Dean reaches out to grab his arm and pull him inside.

The room is dim, illuminated by a soft lamp next to the couch. A book is laying face down on the coffee table next to a glass of amber liquid. Castiel wonders if it’s whiskey, and if he’ll be lucky enough to taste it on Dean’s tongue tonight.

Dean shuts the door behind him. Castiel turns back around to find Dean with his hands on his hips, eyeing the pattern of blood on Castiel’s coat.

He’s not sure how to start explaining what happened. Would Dean bother hearing him out or would he just call the cops? Would he even care that the people Castiel killed were awful, horrible people, or would he yell at him for showing up covered in blood? He deserves it. Coming here was a mistake and Dean should tell him that. Should scream it in his face.

He doesn’t do any of that.

“Is that yours?” he asks.

Castiel shakes his head.

Dean wipes a hand over his mouth. “Alright. Come on.”

Castiel isn’t sure what Dean has planned, but follows him back to the bathroom. Dean guides him in and disappears, returning quickly with an empty laundry basket. He fishes out a washcloth from under the sink and hands it to Castiel.

“Put your clothes in the hamper and get in the shower. Use whatever you need. This,” Dean points to a blue towel hanging on the rack next to the shower, “is clean. Use it.”

Castiel looks down at the cloth in his bloody hands. A murderer like him must look so out of place in Dean’s clean, homey apartment.

“Dean, I—”

Dean holds up a hand. “Stop. Whatever it is, I don’t want to hear it.”

When Castiel looks up at Dean, his eyes are hard and unforgiving. He wonders how long it will take before Dean finally throws him to the curb and tells him to never come back.

“Just get cleaned up.”

With that, Dean turns and walks out of the bathroom, closing the door behind him.

Castiel half expected Dean to either freak out or yell at him over showing up on his doorstep in his current state. Never had he thought Dean would tug him inside and order him to shower.

With a little hesitantion, he does as he’s told. He empties his pockets onto the sink and strips off his clothes, layer after layer, until he’s standing naked in the bathroom. He avoids the mirror, knowing the word _murderer_ will be painted in blood across his face.

It takes a little time to figure out how to turn on the outdated shower, but once he’s standing under the spray of hot water, he sighs, and feels the sorrow finally take hold of him.

He never liked killing people. Even when they were rapists or child molesters or someone equally as terrible. If it were up to him, he’d hand them over to the law and let the court system and people in prison make their lives hell. But when Michael gives an order, it has to done. When he demanded the death of the pawn shop owner and whoever works for him, all Castiel could do was accept it and move on.

When the tears start to come, he’s more angry than anything. He’s not crying because he’s sad that he killed those men, he’s mad because he had to. He didn’t have a fucking choice. He gave up having choices and opinions when he became Michael’s right hand man, thus ridding him of any voice he thought he had before. He’s crying because he could have lived the life of a normal person, but instead, he’s just a walking serial killer.

A few noises escape him. Hushed, pathetic whimpers as he tries to regain his composure.

He can feel the water pressure all the way down in his bones and focuses on the heat instead. He wants to stay here until the water runs cold, but he remembers that Dean probably has to pay for such a luxury and gets a move on. He lathers up Dean’s soap and washes himself. It’s the same brand Castiel uses, just a different scent. He washes his hair too because the shampoo smells so good and he hadn’t noticed the scent on Dean before. He’ll have to pay closer attention.

Once everything is scrubbed clean, he turns off the water and opens the curtain. The clothes basket is gone and there are new clothes waiting for him on the sink. He didn’t even hear the door open or close and wonders if Dean heard those little broken sobs he let out.

He dries off and unfolds them to discover an old t-shirt and a well used pair of plaid lounge pants. They smell of laundry detergent and a little of Dean’s cologne.

He dresses in them quickly, not wanting to keep Dean waiting any longer. When he walks back out to the living room, he finds Dean on the couch again with the book he had been reading before Castiel interrupted him. An ice pack sits innocuously on the table.

When Dean notices Castiel, he looks up and sets his book back down. “Better?”

Better to be dressed in soft, comfortable clothes from Dean's closet instead of his dirty, bloody suit and coat? “Yes, much.”

“Good.” Dean nods toward the empty side of the sofa. “You wanna tell me what happened?”

Dean’s words are kind and open. He’s not demanding that Castiel tell him, but he probably hopes that Castiel does. He sits next to Dean, almost close enough that their knees bump. Castiel notices that Dean doesn’t flinch or tense up and calls it a win. “I took a few lives today.”

Dean pauses. He leans over to grab the ice pack and captures one of Castiel’s bruised hands. He presses it against his knuckles gently. “Did they deserve it?”

“They always deserve it, Dean. Like I told you before, I only kill people if I believe the world would be a better place without them.” _But it doesn't make killing them any easier,_ he wants to say.

He might be a murderer with a coveted position in a mafia, but he doesn’t kill people every day. He hadn’t taken a life in nearly two years. He’d beaten and broken and sliced through people during that time, but he left all of them alive.

“What kind of people were they?”

“Pedophiles. They were...” the words are difficult to come out, “filming and selling videos of young girls.”

Dean’s eyebrows raise. “Oh, so when you say bad people, you mean _bad_ people.”

Castiel isn't sure what kind of people Dean thought he killed, but agrees. “Yes, Dean. We specialize in sex criminals and drug manufacturers.”

Dean lets out a quiet chuckle. “So you hate creeps and Walter White, huh?”

Castiel shrugs. It’s not the best way to put it, but he’s not entirely wrong. He looks around at the room they’re in, the walls covered in memories and sentiment. How had Castiel never gained such possessions? “Where are my things?”

“Your coat is soaking in cold water and the rest is in the laundry.”

His coat is soaking. Dean’s trying to save it for him. Castiel was just going to throw it away because he had never been successful in getting blood out of his clothes before, but Dean is taking on the work load of getting the stains out for him.

Dean welcomed him in to clean up, to take care of his soiled apparel, and to ice his hands. He’s still holding on to the one he grabbed earlier. He didn’t yell or curse or even say anything that indicated he was judging Castiel. He didn’t get angry. He didn’t toss Castiel aside to fend for himself. He had simply accommodated for him.

“Why are you being so nice to me?”

Dean looks at him like he doesn’t understand the question, or maybe he doesn’t understand why it's being asked. “I figured I owed you one when you let me live after I lied to you. This doesn't completely repay you, but it’s a start.”

“Dean, you don’t owe me anything.” Castiel never actually planned on killing him anyway; if anything, he would’ve just banged him up and left with a firm warning.

“I know you don’t think so, but I do. I’m not sure I’ll ever get the chance to save your life, but I figured maybe cleaning your stuff and giving you some donuts might help.”

Castiel smiles. “Donuts would definitely clear your debt.”

Dean returns his smile. He’s so beautiful when he lights up. Castiel wishes he would do it more often around him.

Castiel inches closer, just a little, until his knee hits Dean’s. It’s not enough. He wants to reach out and wrap his arms around Dean and kiss him and kiss him and kiss him. He hates that he can’t, not right now. “Thank you, by the way. I appreciate it.”

Dean looks down toward their knees and swallows. “Are you safe to go home? Would you want to... spend the night?”

Not need. Want. Dean is asking Castiel if he wants to spend the night. He does, he definitely does, but his whole body is telling him that it’s wrong, he can’t, he shouldn’t. Not this time, at least. Not yet.

Dean looks back up at Castiel and he can see that Dean is holding his breath for the answer. And, lord, Castiel wants to say yes, wants to lead him to bed, wants to undress Dean and lay him down, wants to spend the entire night being pressed up against one another. He just can’t bring himself to do it after the night he’s had. It would be unfair to Dean if Castiel were to stick around only to be withdrawn.

“Not tonight, I should actually get going.”

Castiel can see the disappointment in Dean’s face. He wants to kiss it away and promise to stay as long as Dean lets him, but he can’t. There’s so much he can’t do right now and he hates every bit of it.

The two of them stand. Dean walks him to the front door. It wasn’t even half an hour earlier that Castiel stood on the other side of that door. He wishes he could stay longer; maybe get tangled up under the blankets of Dean’s bed, maybe wake up in a confusion of limbs, maybe share morning breath kisses.

He’s always been good at wanting what he can’t have. While he can have Dean whenever he wants, it isn’t about taking. It’s about waiting to receive. He never wants to make Dean feel that he’s pushing or forcing him to do anything, doesn’t want him to be scared to reject Castiel, doesn’t want him agreeing to something he doesn’t want because he thinks it’ll save his life.

He wants Dean to want him. He’s just not sure how they get to that point.

Dean stands before him, holding the door open, but not saying goodbye. Castiel watches his line of sight drop from his eyes to his lips and prays that Dean closes the distance.

He doesn’t. Of course he doesn’t. How could he want that?

Sad and a little let down, Castiel leans in to peck his cheek. Again. He wonders how many of these awkward not-kisses they have to share before something breaks.

“Have a good night, Dean.”

He walks out before Dean responds, too afraid he’ll break his heart instead of filling it.


	6. Chapter 6

“Dean?”

Dean looks up from the dough he’s kneading to find Claire with her head stuck around the swinging door from the lobby. “What’s up?”

“Some guy wants to talk to you.”

Jesus. If Dean had a nickel for every time someone wanted to talk to him, he wouldn’t have to talk to anyone anymore. He sighs. “I’ll be out in a minute. He’s not mad or anything, is he?”

Claire shakes her head. “No, just bought a coffee and asked for you.”

“Great,” Dean mumbles, but Claire is already gone.

Whoever it is, is going to have to wait for Dean to finish with the dough. He folds it over on itself and palms it until it’s a little less sticky and more elastic, throwing pinches of flower on it as he goes. Once it’s at the right consistency, Dean rolls it around in the oiled bowl, wraps it up, and sets it in the proofing cabinet.

He pastes a smile on his face. It hasn’t been a particularly hard day—most days aren’t. Most days, Dean takes his time, goes at his own pace, takes a long lunch, and makes sure to sit down for a few minutes every couple hours. It’s not actually that hard working six days a week when it’s something he loves so much and the work isn’t all that difficult. But he definitely has to go out there and pretend that he didn’t wake up at 5:15 and proceed to not drink enough coffee to lift his sleepy mood.

Dean pushes through the door. Claire gestures vaguely at a table to Dean’s left.

Castiel is there, sitting at the same table he chose that day he came in to proposition Dean for their first date. He’s staring out the window with his chin set on his fist.

It’s been almost an entire month since he’s seen Cas. The last time he’d shown up, it was mid-August and he was covered in blood and bruises and something inside Dean had lit up like a match being thrown on a log soaked in gasoline.

Cas had come to him, god knows why, after a night of killing people, looking absolutely  wrecked . Not because of the blood or dirt or blackening knuckles, but because he just looked so incredibly sad. His eyes were hooded with sorrow, his voice low and on the verge of breaking around each syllable.

Dean hadn't been happy to find him there late at night, just before he was about to go to bed, but he took care of Cas anyway. He put him in the shower, soaked and scrubbed and soaked that stupid jacket of his, and iced his hands. He wanted nothing more than to make everything alright for him.

By the end of the night, Dean asked Cas if he wanted to stay, and Cas politely declined and left as soon as he could. When he didn’t come around again for such a long time, Dean figured he’d finally come to his senses and dropped him. Cas is probably better off dating someone in his own line of work anyway.

And yet, here he is, sitting in Dean’s café like it had only been yesterday.

Dean approaches his table, drawing Cas’s attention away from the passers by outside the window. He smiles.

“Hello, Dean.”

Hello, Dean?  _Hello, Dean_ _?_ Cas pops back into his life for the first time in a month and gives him a  _Hello, Dean_ like everything is fine?

“Cas.” His reply is tight lipped. He sits down stiffly.

Cas crosses his arms over the table. “How has your day been?”

Dean should have smacked himself for being so stupid to expect Cas to apologize for his absence. Did he even care? Did he think that Dean wouldn’t worry about him? Wouldn’t want to see him, or even hear from him at the very least?

“It's been alright.”

“Hm,” Cas hums. He leans forward to pick the sharpie off Dean’s apron again and starts writing another address on his coffee sleeve. “Mine was boring. But it's definitely better now.” He looks up to wink at Dean, then gets back to the sleeve. “I’d like you to take a personal day tomorrow. I’ve made a reservation for us.”

Cas slides the sleeve across the table to Dean, who looks down at it like it had offended him.

“A reservation?”

“Yes. There’s this Italian restaurant near my apartment that I enjoy and I’d like for you to join me there at 8 tomorrow.”

Dean can feel his blood starting to boil. What gave Cas the right to walk in and out of his life like it was a fucking Taco Bell? With no consideration, no regard for Dean’s schedule or opinion, not a single fucking word in his absence. 

“I’d appreciate it if you actually took the day off instead of ignoring my request like you did last time,” Cas continues, oblivious to Dean’s irritation. “If you need incentive, I’d be happy to arrange some appointments to keep you busy and out of work for—”

And that’s it. He’s fucking  _ had it. _

_ “ _ _ Stop.” _

Cas draws back and looks like he's about to retort, but he stays shut up.

“Just stop, alright? I’m sick of this shit.”

It takes a moment, but Cas’s face drops. He looks just as dejected as he did that night he showed up a month ago, and Dean realizes a second too late that his statement may have been misinterpreted.

Dean sighs and scrubs a hand down his face. “Look, I like going out with you, but this has to stop. You can’t just come in here and tell me where we’re going without even asking if I’m free first. That’s not how dates work.”

Castiel’s face shifts to one of confusion. If Dean weren’t mad at him, he’d call him cute and press a thumb to soften the crease between his brows.

“I need equal footing in this, man. We can’t just do whatever you want to do all the time, whenever you want to do it. If you want to make plans for us, that’s fine, but you gotta  _ ask _ me if I want to go on a date, you can’t just assume.”

Cas looks at him like the thought never once crossed his mind. Dean wonders if he’s being too hard on the guy, because he did say that he hadn’t dated in a long time. Maybe he truly didn’t know this is bad form.

But it doesn’t stop Dean from surging ahead. “And while I’m at it, I’m pissed at you. You say you like me, but then you disappear for weeks on end. You don’t even call to tell me you’re alright. You can’t just show up whenever it’s convenient for you and leave me hanging in the meantime. I’m glad you trust me enough to show up after you—” Dean stops himself, suddenly remembering they’re in the middle of a café and people can hear him. He coughs awkwardly and lowers his voice. “Like you did last time. If you ever need me like that again, I’ll be there for you, no questions asked. But I need a little warning, Cas.”

Cas is chewing on his lip, staring at the table like a scolded puppy. Dean wants to cut him a break, because his heart hurts when Cas looks like this, but if he doesn’t get it out now, he might not ever.

“You’re right,” Cas concedes. He meets Dean’s eyes. “I’m sorry.”

Dean will go easy on him—in a minute. “You like me, right? You want to make this work?” He stops just long enough for Cas to nod before continuing. “I want your phone number. I want a minimum of one phone call a week. I want to see you more than once or twice a month. And no more fancy, expensive restaurants—any place with more than one fork is off limits.”

Cas all but rolls his eyes. “Dean, don’t you think that’s a little—”

Dean raises a finger. “ _Off _ limits. So cancel that reservation. You want to go out tomorrow? We’re going to the Roadhouse. Ten o’clock, no black ties allowed. You’re going to drink cheap whiskey and  _ like _ it.”

Cas sighs through his nose. Dean holds his breath, waits for Cas to tell him to fuck off or rejects his idea. But Cas reaches for the coffee sleeve. On the back, he writes out ten digits and gives it back. “Send me the address. I’ll be there.”

Once again, Dean stares down at the sleeve. He didn’t expect that speech to actually work.

But that’s the thing he’s learning about Cas—he’s not going to off him for having an opinion. He doesn’t scare easily, and he’s not going to walk away just because Dean has some words to share. He actually sat there, listened, apologized, and followed through. When was the last time someone did that for Dean?

Dean nods. “Alright. I have to get back to work. I’ll see you tomorrow.”

They both stand and Dean awkwardly glances at Cas, not sure how he’s supposed to say goodbye. Should he stand around and wait for Cas to kiss his cheek again? Lean in to hug him? Shake his hand like they just had a business transaction? None of these options seem right.

Cas makes the decision for him, though, and gives him a curt nod before walking out of the café.

There he has it: a scheduled third date with a mobster. He pushes his fingers through his hair and backs into the kitchen before he can think too much about it.  


— — —

A day later, a cab is dropping him off in front of the roadhouse. He’s freshly showered, beard trimmed, and dressed in his favorite jeans and a plaid shirt. He stood in his closet half an hour ago, debating whether to wear his lucky flannel, but decided against it at the last minute. Would he even need it? This might be their third date, but the chances that they’ll participate in post-third-date traditions are pretty slim.

That doesn’t stop him from being nervous, though.

When he steps out from the cab, he sees Cas standing outside the Roadhouse’s door. He looks much like he did that day they went to the park, with dark jeans and a Guns N’ Roses shirt under a black leather jacket. He spots Dean, too, and unabashedly checks him out.

“Glad you made it,” Dean says when he walks up to Cas.

Cas smirks something sultry. “I did say I’d be here.”

God, the things Dean wants to do to wipe that smile off his face. But he can’t do any of them in public, so he just reaches out to grab one of Cas’s hands. Halfway there, he realizes just what holding Cas’s hand would mean.

It would mean walking into the roadhouse as a couple. Coming out to Ellen and Jo and Ash. Making this thing between the two of them more physical and real, solidifying the concept he already had trouble accepting. It would mean no going back, jumping in feet first without a life jacket. Is he prepared for that? Is he ready for whatever level of commitment came from something as trivial as holding hands?

He almost pulls back, but Cas meets him in the middle and laces their fingers together. And suddenly, it doesn’t feel so scary anymore. Cas’s hand is a warm comfort.

“These look a lot better,” Dean says when he notices Cas’s hand is back to its normal complexion.

“Thanks to you.”

Dean doesn’t believe him. He only had the chance to ice one of Cas’s hands for a few minutes before Dean asked him to stay and Cas practically ran out at the idea.

Instead of deflecting, he pulls on Cas’s hand and leads him inside the bar.

It’s a Saturday night, so the place is hopping. Around the roadhouse, Dean finds people shooting pool, drinking, singing, and laughing. He’s searching for some empty seats when Jo calls his name from behind the bar. Dean smiles at her and she waves them over to two unoccupied stools at the counter. He pulls Cas in tow as he heads over to her.

“Where have you been?” she yells over the music. “I haven’t seen you in forever!”

Dean and Cas take their seats and he shrugs. “Been kinda busy, kiddo.”

She rolls her eyes at him and turns her attention to Cas. “Who’s this? Aren’t you going to introduce me?”

Dean's heart thumps a few times, reminding him that Jo still thinks he's straight and this is his first time bringing a man back to the roadhouse. Well, he brought Benny while they were dating, but he made sure they kept on separate sides of a booth with a zero-tolerance policy of PDA.

“Cas, this is Jo. Jo, this is Cas, my... date.”

Jo reaches across the bar and shakes his hand. “Nice to meetcha. What are you two drinking?”

Dean stares at her, eyes wide. That was all, just  _ What are you two drinking_. No outburst of laughter, no anger that it took him so long to tell her, not even a hint of sarcasm. 

Jo is looking between them expectantly. Dean clears his throat. “The usual, for both of us.”

Jo grabs a few glasses and sets them down on the counter. The usual is just well whiskey and she pours each of them a double. She winks. “You two behave now.”

She skips off to help some other customers, leaving Dean grinning next to Cas. He turns to his date to find him holding the glass up, staring at the liquor.

“My shoelaces are probably more expensive than this whole bottle.”

Dean smiles even wider. “ _ Exactly _ . Cheers!” He clinks his glass against Cas’s and takes a a healthy swig. Cas does the same and grimaces.

“I’m not convinced this isn’t poison.”

Dean laughs. “Less thinking, more drinking.”

Cas scoffs, but takes another drink. He kicks Dean under the bar and Dean kicks him back, both of them chuckling.

Someone smacks Dean on the back and he doesn't even turn around to know who it is. He smiles wide, and before he can come up with something clever to say, she cuts him off with, “Jesus, Lord in Heaven, I thought you were mad at me or somethin’.”

Dean swirls his stool around to face her. “Ellen,” he rejoices and stands to hug her.

She stops him with a hand to his chest. “Hugs are for people who pay my bills. And  you haven’t been here lately to help pay said bills.”

Her drawl is friendly and familiar and feels a little like home. “Oh, come on, Ellen. God knows I was singlehandedly paying your rent about this time last year.”

“Yeah, so you got some making up to do.” She pushes him back down onto his stool and nods her head at Cas. “Who’s this handsome devil?”

Cas straightens up. “Castiel,” he introduces, holding out a hand.

She gives it a shake with, no doubt, one of her firm, Southern grips. “Ellen.”

She regards him for a moment too long and Dean feels the back of his neck heating up. He knew Ellen didn’t have a problem with same-sex couples—hell, she’d put up a little gay flag when marriage was legalized in 2015, right up next to the line of tap beer. But she was always good at scrutinizing people Dean was interested in. Her and Lisa got into a fight the first time they met and Lisa never came back.

But Cas is meeting her gaze, still shaking her hand, like he knows exactly what her game is.

When she pulls her hand back, she looks over at Dean again like the mini staring contest she had with Cas never happened. “How about a couple’a burgers? My treat.”

That’s Ellen language for _ I approve_. He smiles. “Gimme the works.”

She looks at Cas, who pipes up, “Deluxe, please.”

She claps them both on the backs and gives Dean a toothy grin. “I’m glad y’all made it in. Makes me happy to see you gettin’ back out there, Dean.”

She walks off toward the kitchen as Dean’s cheeks flush. He was hoping she wouldn’t mention it. He chances a glance at Cas, who’s face is expressionless.

“What?” Dean challenges.

“Finally getting back out there?”

Dean taps the bottom of his glass against the counter. “Yeah, uh. I haven’t dated anyone in a couple years.”

Cas tilts his head. “Why not?”

He shrugs. “I don’t know. I never really liked dating a whole lot to begin with. Whenever I wanted company, I’d just go out and pick someone up. Some of ‘em stayed, most of ‘em didn’t.”

“I don’t understand why any of them wouldn’t stay.”

The way Cas says it, with such honesty and confusion, breaks Dean’s heart a little. He’d never admit it to anyone else, but it gets lonely out here sometimes. He works his ass off for nice pay checks and doesn’t have anyone to spend them on. Most nights, he’s found on the couch either reading or drinking beer to a TV show on Netflix. His apartment and his bed are perpetually empty.

And Cas is looking at him, with those big blue eyes, like Dean deserves more. Like it’s unfair to him.

It’s all a little too much, so he swallows down the remaining liquor in his glass and plays it off, like he does everything else. “I don’t know why you’re complaining. It just means that I’m single for the taking.” He throws a wink at Cas.

Cas rolls the bottom of his glass in circles on the table, staring at it. “If you don’t like dating, why are you letting this happen?”

Dean can’t tell if Cas is fishing for compliments or trying to give Dean an out. But, that’s kind of the point. That’s why Dean is “letting” this happen. Because Cas isn’t like anyone else he’s ever met before. Not just in the  _ he’s powerful and dangerous _ way, but because he’s kind and gentle. Because when he has a bad day, he goes to Dean for comfort instead of taking his frustrations out on him. Because he’s straightforward without being rude. Because he could easily be an asshole, but he makes a noticeable effort to be a good person.

Because there are people Dean has met who aren’t murdering mafia members, but have worse character than Cas.

“You’re not like them,” Dean settles on saying.

Cas pops his eyebrows. “I’m not sure if that’s a good thing or a bad thing.”

Dean smiles. “It’s good. Definitely good.”

Cas hesitantly mirrors Dean’s expression and his whole body starts to buzz—and not from the drink he downed.

Before long, their burgers come, and they chow down. Jo spends plenty of time with them, enough to where some of the patrons are visibly—and verbally, sometimes—upset about it. She asks Cas lots of questions, like what he does for work (“I'm an executive assistant.”) and how old he is (“Thirty-five.”) and what he likes to do in his spare time (“I enjoy puzzles. Mostly crosswords and sudokus.”). Eventually, when she probably decides that Cas isn’t some crazy axe murderer (oh, the irony), she gives him her own version of the staring contest. Cas wins that one.

When she finally leaves them be, Dean and Cas practically roll over the bar in a fit of laughter. The whiskey is just starting to kick in, and Dean finds himself leaning a little too far and having to grab Cas’s shoulder to push himself back up to the right position. His hand lingers there, but he doesn’t suspect Cas notices.

They spend the rest of the night like that: drunk, happy, a little closer than usual. At some point, Dean’s hand finds its way to Cas’s knee and when he realizes it, he doesn't pull back. He gives a little squeeze, which earns him a smile, and Cas’s foot knocks into his again.

Dean loses track of how many drinks they have somewhere between Jo telling Cas the horror story of when Dean found out the girl flirting with him one night wasn’t free and becoming mesmerized by Cas’s profile in the low lighting. He’s beautiful, absolutely stunning; which are the kind of words Dean never uses to describe a man, but there’s something so incredible about the straight line of his nose and the sharp angle of his jaw and the softness of his lips.

It would be so easy to cup Cas’s chin in one hand and pull his face close, to feel those lips for himself somewhere other than his goddamn cheek. He wants to be kissed by Cas all over, again and again, and then return the favor.

His mind is starting to wander to dangerous territory for a public place and he regains control of his thoughts just in time for Cas to turn to him, laughing with complete abandon, and all Dean can think is,  _ Shit_.

When the bar closes at two, Ellen and Jo kick everyone out except Dean and Cas. Ash finally emerges from the kitchen, complaining that he hasn’t gotten in his daily nap. Ellen pours a shot of some good stuff for all of them. Dean has already paid their tab—after arguing with Cas over the bill, declaring that since Cas has paid for their first two dates, it’s only fair that Dean gets to pay for this one—but it's tradition that when Dean stays long enough to close down the bar, he gets a free shot. They each take a glass and hold it in the air.

“I don't have anything to toast to,” Ellen says, “so let’s just toast to everything. All of it. Cheers.”

They each clink their glasses against one another and throw back their shots. The burn in Dean’s throat is softened by his intoxication, but he can taste the sweetness of it, much different to what he’s been drinking the whole night. All of them let out  _ ah _ s of satisfaction at the sting.

Ellen pours one more shot for herself and downs it. She picks up the handheld next to the cash register. “Alright, you two, get the hell out of my bar.”

Dean lets out an exaggerated groan. “You can’t kick us out, we’re paying customers!”

“Yes the hell I can, and you will  _ not _ argue with me, mister.” She puts the phone up to her ear. “Now get on out of here, I’m calling you a cab.”

Dean gives a noise that’s a cross between a grunt and a laugh, but stands. He wobbles on his feet and attaches himself to Cas’s shoulder for balance.

“ _Whoa_.” Dean draws out the word, his whole head dizzy.

Cas stands, much more gracefully than Dean had—did Cas drink way less than Dean or could he just handle his liquor better?—and ducks under his arm to hold Dean up. He’s chuckling low in Dean’s ear, the sound raising goosebumps on his arms. “Let’s get you home, Dean.”

“Okay,” he quietly agrees. He turns to Ellen, talking to a cab company, and Jo wiping down the counter where Dean and Cas had been sitting. He tries to wave goodbye but ends up just flapping his arm around in the air like a toddler. “Bye, guys.”

They return the sentiment and Cas gives them a few grateful words that Dean can’t understand because his vision (and hearing, apparently) has zeroed in on the door they’re heading toward. Cas opens it for them when they get there and hauls Dean through.

Outside, the world is quiet and dark and chilly. Cas is pressed up against Dean’s side, all warm, all solid, all absolute. His arm is wrapped around Dean’s middle. It feels so natural, to be leaning against one another, despite this being the most they’ve ever touched each other before. Dean hopes it won’t be the last time.

The thought crosses his mind, though. It surprises him just how frightened he is at the prospect of never being able to touch Cas again. As if, if he didn’t take the chance now, he might not ever be able to again.

He turns Cas toward him, taking both of his jacket lapels tight in his hands. Even in the dark, Dean can recognize the same shades of blue he saw that first night Cas came crashing into his life. “Had a good night with you.”

Cas takes half a step closer and Dean’s fists are pressed up between both of their chests. “Me too.”

Dean riles up every ounce of courage he has to ask, “Come home with me?”

Cas bites his lip, gaze dropping to Dean’s mouth. He almost looks like he’s going to kiss Dean, but then Cas meets his eyes again and he nods. “Okay.”

He’s so close that his breath washes over Dean’s face and he smells of whiskey. That’s all Dean needs to pull Cas in by the jacket and end the torturous game of waiting for Cas to make the move. He makes it himself, goddammit, and when he does— _ fuck _ .

Their lips meet somewhere in the middle. Cas lets out a small, broken sound, and his mouth is  _ soft, soft, soft._ It’s so much better than Dean thought it would be. Cas is kissing him like he’s waited decades rather than just a few months. His hands come up and grab at the back of Dean’s neck, tangle in the short hair at the base of his head.

Dean can’t get enough of it. He crowds in closer, wrapping his arms around Cas’s waist and pushing his chest flush against Cas’s. It’s all too soon and not soon enough when Cas’s tongue starts licking into his mouth, and Dean moans into the kiss without shame.

There’s a feeling of  _ right_, a feeling of  _ finally_. Like the world around them had been holding its breath and finally exhaled. Dean sighs with it.

There’s a horn honking, and Cas pulls away from Dean. He doesn’t stop the whine that comes from the back of his throat.

“That’s our ride,” Cas informs him.

Dean looks over and, sure enough, a taxi is honking at them impatiently. Begrudgingly, he unwraps himself from Cas and allows himself to be lead to the waiting car.

Dean gives the driver the address. Logically, he knows that he shouldn’t be rude enough to make out with Cas in the backseat, but he just looks so inviting and goddamn kissable, it’s hard to resist.

In an attempt to be considerate, Dean settles for intertwining his and Cas’s fingers on the seat between them. He looks up to Cas, who is staring at him with something in his eyes that looks like fondness, like affection.

Cas slides across the seat until their thighs are pressed together. He noses up under Dean’s jaw and starts to lay quiet, delicate kisses against his neck.

Dean leans his head back against the seat, granting Cas better access, and takes a moment to just  _ feel _ for a little bit. There’s the hazy buzz under his skin, Cas’s lips on his neck, the sensation of floating he’s getting from riding in the car. The elation of Ellen and Jo’s acceptance. The relief of the kiss.

He could fall asleep if he’s not careful, so he picks his head back up and throws consideration out the window. His mouth is on Cas’s again in an instant, taking him by surprise. Cas gets with the program quickly enough, though, and frames Dean’s face with his hands, lips synchronizing.

Dean wants nothing more than to lean him back in the seat and start stripping him, but he’s sure that would probably get them kicked out. Cas’s hands are moving all over him, though, across his chest, down his arms, over his thighs, up his back. He leaves Dean’s skin tingling in their wake, his whole body flushed and hot.

The car finally— _ finally _ —stops in front of Dean’s building, and the driver barks the total at them. Cas hands him some cash, how much Dean isn’t sure since it’s so dark, but he must be satisfied because he doesn’t protest. Dean pulls him out of the car and nearly runs to the door.

The make it up the stairs in a fit of giggles and roaming hands. They stop a few times to share kisses and it’s a freaking miracle they even get down the hall to Dean’s apartment.

Dean shoves Cas against the door and kisses him insistently as he digs the keys out of his pocket. He blindly fumbles with the ring and guesses where the lock is, because he’ll be damned if he pulls away from Cas to unlock the door he's had for five years.

He manages to stick it in and turn the deadbolt. They both spill inside and Dean barely has a chance to shut the door behind them before Cas is on him again, pushing him up against the door, kissing him.

Dean pushes Cas’s jacket off his shoulders and flips them around so Cas is against the wall. Cas’s hands have made their way under Dean’s shirt and are clutching his hips, fingers digging in in all the right ways. Dean groans and kisses down Cas’s cheek, past his jaw, until he’s mouthing at his neck and collar.

“Dean...” Cas sighs. His hands move up to Dean’s back, nails scraping lightly.

Cas rolls his hips into Dean’s and lets out a filthy noise. They’re both hard and panting and pulling at each other, tugging at shirts, unbuttoning pants. Dean could spend forever in this moment, drinking up every ounce of sound Cas made, soaking in the way his hands move over Dean’s body.

“Dean.” Cas’s voice is half begging, half demanding, and it makes Dean whine. “Dean, stop. We can’t.”

Can’t? Dean’s been wanting this for weeks, maybe even months, maybe since the first moment he laid eyes on Cas. He’s waited, he’s been patient, and now he’s being told he can’t and it makes him nearly fall to his knees.

But he pulls back to look at Cas’s face, who seems just as disappointed. “What’s wrong?”

It’s cute, the way he looks so sad and miserable, and also disheveled with his clothes half off and a stiffy tenting his pants. “Not tonight, not like this.”

It takes Dean a little too long to process what he means, but when he does, he leans in to kiss Cas’s forehead. They’re both a little too drunk and this is moving a little too fast. It wouldn’t be such a bad idea to slow down.

“Okay,” he agrees. “Not like this.”

“I want this,” Cas explains. “I really want this. But I need to know that it’s  you calling the shots, not the whiskey. And not the fear.”

“The fear?”

Cas looks like he could cry. His finger traces Dean’s collar bone tentatively. “I don’t want you to go along with any of this because you’re scared of me.”

And Jesus Christ, it clicks in Dean’s brain that Cas  _ himself _ has been scared this entire time. Scared that Dean didn’t actually want any of this, that Dean was only going out with him because the alternative was dying. Oh, god, how wrong he is.

Dean pulls him in to a tight hug. “I don’t do anything I don’t want to do. You can’t scare me into liking you.”

Cas wraps his arms around Dean’s middle, slipping one hand under his shirt and splaying on his bare back. “You like me?”

_ What an idiot_ _,_ Dean thinks. He kisses Cas’s temple. “I wouldn’t be doing any of this if I didn’t.”

In the crook of his neck, he feels Cas smile and press his lips to the skin there. It sends a shiver down his spine, but not in the sexy way. More like in the _ I want to make him happy _ way.

“Come on,” Dean insists, untangling himself from Cas’s grip and taking his hand. “Let’s go to bed.”

Dean leads Cas back to the bathroom where he finds the spare toothbrush under the sink (the one he bought after Cas’s last visit because he figured he’d need it sooner or later) and hands it to Cas. The smile he gets in return could singlehandedly power the sun itself.

With clean teeth and a couple aspirin popped, Dean and Cas shuck out of their pants and fall into bed with just boxers and t-shirts. Dean pulls the blanket over them and scoots closer to Cas, draping an arm around his waist. Cas works an arm under Dean’s head and tugs his face into his chest, sighing quietly.

Dean’s whole body is humming blissfully. The whole night went so well, despite his initial nervousness. Ellen and Jo barely mentioned his blooming relationship with Cas, they got drunk and merry, they connected for that long awaited first kiss. And now, Dean is pressed up against Cas, feeling lucky and delighted and satisfied.

Cas cards his fingers through Dean’s hair, making him lean into the touch. “Will you still like me in the morning?”

The way he says it is so innocent that Dean could almost forget who he is outside of his presence. With his head against Cas’s breast, he listens to the steady beat, the reminder that Cas is only human, he’s not immune to the emotions of the average person, and he smiles.

“Yes. Now shut up and go to sleep.”

And so they do.


End file.
